Migration in the Early Chesapeake: Dorchester Co., MD, as a Case Study, 1650–1750

Abstract

This article examines the migration patterns that shaped the early settlement of Dorchester County, Maryland. Dorchester County is located on Maryland’s Eastern Shore, an area distinctive in terms of its geography, history, and culture. In U.S. history, migration has generally proceeded from eastern areas to western ones and from northern areas to southern ones, a pattern dating back to the earliest colonial settlements. Settlement in Dorchester County proceeded primarily from east to west and south to north, with additional migration streams coming from the north out of Delaware and from the west out of Somerset County. This gave Dorchester County an unusual historical dynamic because of the different socio-cultural and religious backgrounds and settlement patterns from the regions in which those migrants came. The Eastern Shore’s geography, shaped by an extensive coastline and major riverways, contributed to this settlement pattern, for the Chesapeake Bay region, with its complex network of rivers and streams, forms one of the world’s three largest natural estuaries. In terms of genealogy and family history, this mix of settlers importantly shaped the cultural dynamics of the Eastern Shore, leading to complex family histories that blended different cultural, religious, and linguistic influences. Free European-American settlers dominated migration into early Dorchester, but unfree laborers, including slaves and, early on, white indentured servants, came to Dorchester in substantial numbers along these same routes and made important contributions to the cultural development of Dorchester and surrounding areas. In later years, out-migration from the Eastern Shore took settlers of all backgrounds throughout the growing United States and carried the influence of the Eastern Shore to the south and west as well as into the urban areas of the northeast.

1. Introduction

The statement “Go West, young man” has often been associated with the overall thrust of migration in United States history. The words are attributed to Horace Greeley, well-known editor of the New York Tribune, although this may have been a paraphrase of a statement John B. L. Soule made in 1851 (Taylor 2015). Whatever their source, they express the predominant popular thinking about the overall course of migration in U.S. history. The west as a concept, linked with the American frontier, has occupied a central place in historiography as well as in the imagination (Turner 1893; Billington 1956; Billington and Ridge 2001; Limerick 1987).

Historically, this east to west pattern tends to have been the case, with migration paths following the expanding frontier. During the colonial period, British immigrants to the North American colonies settled along the Atlantic coastline. Port cities along major interior waterways like New York, Philadelphia, Charleston, and Savannah became critical colonial ports of entry. The “east to west” narrative in many cases masks a more complicated reality often shaped by particular local circumstances, geography, and relations with native peoples, among other causes.

This study examines the settlement of early Dorchester County, located on Maryland’s Eastern Shore. The Eastern Shore, which today includes parts of Delaware, Maryland, and Virginia, known over the course of the last century as the Delmarva peninsula, is a narrow body of land extending from the southeastern region of Maryland and Delaware southwards into the Chesapeake Bay. Two Virginia counties, Accomack and Northampton, form the lower portion of the peninsula and comprise most of the eastern shore area of the bay region. Parts of Somerset, Worcester, and Dorchester counties in Maryland comprise the lower Eastern Shore and the northern boundary of the Chesapeake Bay. On the western side, several smaller peninsulas, punctuated by the Potomac, Rappahannock, York, and James rivers, shape the distinctive geography of one of the world’s largest natural estuaries, one whose watershed spans 64,000 square miles and includes part of six states and the District of Columbia (Thomas 2004; Curtin et al. 2001; Jones 1925; Torrence 1935).

During the sixteenth and seventeenth centuries, five major groups of Native American peoples lived on Maryland’s Eastern Shore in the area that would become Somerset and Dorchester Counties. The Nanticoke people lived along the Nanticoke River and were among the inhabitants John Smith encountered when he explored the area in 1608. The Choptank people dwelt along the Choptank River in the northern part of Dorchester County and southern Talbot County near present-day Cambridge, Maryland. To the north, near the future boundary between Dorchester, Talbot, and Kent Counties, the Wicomiss people lived in the early seventeenth century. To the south, near what became the boundary between Somerset County and Accomack County, Virginia, lived the Pocomoke people. The Assateague people lived along the Atlantic coast and inhabited some of the coastal islands. Additionally, larger groups often included distinct bands within them, such as the Manokin and Annamessex peoples, both part of the Pocomoke paramountcy. The Manokin people resided in the part of Somerset County that became the town of Princess Anne, and the Annamessex people lived in coastal region that became southwestern Somerset. The Native peoples of the Eastern Shore engaged in fishing, farming, and trade and included Algonquian-speaking peoples, among them the Nanticokes. After the European settlers began to arrive, their numbers declined due to disease, societal disruption, conflict with the European settlers, and relocation. Colonists established Nanticoke reservations along Broad Creek and a Choptank reservation near Cambridge. The names of these Native groups persisted in the place names of the Eastern Shore, however, and, despite their reduced numbers, a notable Native American presence remained in the region throughout the seventeenth century and into the eighteenth century and beyond. By the late 1760s, the Nanticokes had lost their reserved lands to the European-American settlers, but some of the Choptanks retained land into the late eighteenth-century before finally losing rights to it in 1822 (Rountree and Davidson 1997; Morfe 2014, revised 2022).

Giovanni de Verrazano, the first European in modern times known to explore the Chesapeake Bay region, visited the area in 1524. Spanish explorers ventured into the region in the middle decades of the sixteenth-century and established a short-lived missionary outpost among the Powhatan peoples. When English colonists off track for New England sailed into the region in 1607, they chose James Fort, later Jamestown, a secluded island located in the lower bay’s James River as their place of settlement. The Powhatan Confederacy, ruled by Chief Powhatan, father of Pocahantas, dominated much of the region, although Powhatan had limited influence on the Eastern Shore, in part because of the Chesapeake Bay and the distance between the Eastern Shore and the rest of what was to become the Virginia colony. John Smith and others visited the Eastern Shore in 1608, and English colonists began carving out plantations in the lower shore region over the following decade (Perry 1990; Land 1981; Billings et al. 1986; Rountree 1990, 1992, 2005; Russo and Russo 2012; Lewis and Loomie 1953; Gleach 2000).

When English settlers arrived in Maryland in March 1634, they settled on St. Clement’s Island and formed a more permanent settlement shortly afterwards at St. Mary’s City on the isthmus between the Potomac and Patuxent Rivers (Russo and Russo 2012). Over time, Virginia’s Potomac shoreline would become the boundary between the two colonies, later states. From near Reedville, in present-day Richmond County, Virginia, the line would stretch across the bay to Smith’s Island and from there by water to the mouth of the Pocomoke River, which today forms the boundary between Somerset County, Maryland, and Accomack County, Virginia. From there, the line stretches diagonally about twenty miles to the Chincoteague Bay and the Atlantic Ocean on the region’s eastern shoreline.

Figure 1 and Figure 2 show this area today, including the modern boundary between Virginia and Maryland.

But, in 1634, these distinctions lay in the future. Boundaries were vague, and colonists would not clarify the boundary between Virginia and Maryland until later in the seventeenth century. They would not settle the boundary between Maryland and southern Delaware until even later. The Catholic settlers who arrived at St. Mary’s in 1634 under the direction of Leonard Calvert came with a different remit than those who had settled at Jamestown in 1607. While predominately English in heritage, religious, cultural, and political differences initially separated them from the Virginia colonists, and rivalries over land and boundaries characterized much of their early relationship (Russo and Russo 2012; Danson 2001).

2. Literature Review

I situate this study at the intersection of multiple fields of inquiry: early American history, including the Atlantic context; the regional history of the Chesapeake, including work on the Native American peoples of the region; the state histories of Maryland and Virginia (and, to a lesser extent, Delaware); the local histories of Dorchester, Somerset, Talbot, Accomack, and Northampton Counties on the Eastern Shore; and disciplinary studies of family history, genealogy, demography, migration history, geography, and ecology. The following paragraphs briefly examine key works that provided the intellectual foundation for this study.

The work of E. G. Ravenstein (1834–1913), published in three seminal articles between 1876 and 1889 (Ravenstein 1876, 1885, 1889), outlined ten laws of migration that have shaped academic study ever since. One of the principles Ravenstein stressed is that migration often occurs in steps with migrants moving a short distance initially followed by a subsequent migration elsewhere (Conway 1980). Ravenstein also laid the framework for the “push” and “pull” model of migration (Catapano 2025). Later scholars, including Waldo Tobler and his “First Law of Geography,” built on Ravenstein’s work (Lawton 1968; Tobler 1995; Corbett 2003; Miller 2004; Catapano 2025). Ravenstein and Lawton wrote about British migration, and Ravenstein wrote in the second half of the nineteenth century about recent British migration. But the concepts Ravenstein outlined have been applied to migration history more generally in other contexts, often with refinements that consider the effects factors like ethnicity, social class, age, or education may have on the decision to migration or the route or method of migration chosen (Grigg 1997; Catapano 2025). In the context of early America, Bernard Bailyn has written extensively about colonial immigration and migration in the seventeenth and eighteenth centuries (Bailyn and DeWolfe 1986; Bailyn 1988, 2005, 2012). Additionally, numerous local studies examine individual settlements and the factors that drew settlers there (Torrence 1935; Jones 1925). Frederick Jackson Turner outlined the significance of the western frontier in 1893 with what he termed “the colonization of the Great West,” (Turner 1893), and the central role of westward migration in American development has been a key concept in historiography (Billington 1956; Billington and Ridge 2001; Hine and Faragher 2000; Scharff 2002; McDaniel 2014; Catapano 2025).

Methodologically, although not primarily a Chesapeake historian, the work of John Putnam Demos has contributed to this study. Two of Demos’s early works, A Little Commonwealth: Family Life in the Plymouth Colony (1970) and Entertaining Satan: Witchcraft and Culture in Colonial New England (1982) were sophisticated community studies built on the academic study of family history. Demos grounded his study of accused witch Rachel Clinton in a microhistorical analysis of her individual family history, fractured by early death, remarriage, socio-economic change, and mental illness, and its place within local society. He amplified this approach in recreating the social world of the Williams family of Deerfield, Massachusetts, in the late seventeenth, eighteenth, and early nineteenth centuries in The Unredeemed Captive: A Family Story from Early America. Demos chronicled the life of Eunice Williams, a New England Puritan girl adopted into Mohawk society after being kidnapped during a raid on Deerfield. Given a new name and a new identity as a Native American woman, Eunice never permanently returned to her family in New England despite their ongoing efforts for decades. Demos’s approach to the family and community history continued in later works (Demos 2004, 2020) and has influenced scholars including Ellen Fitzpatrick (Fitzpatrick 1983), Rebecca Tannenbaum (Tannenbaum 1997), Jill Lepore (Lepore 2001), Wendy Warren (Warren 2007), Brian Luskey (Luskey 2016), and others. While this article considers a large group of migrants who lived in a county that spanned nearly 700 square miles, I have modeled my approach to family history, social networks, and community relationships after the microhistorical analysis Demos employs.

In looking at migration into and within the Chesapeake region, the works of Phillip Curtin, Grace Brush, George Fisher, and William Thomas (Curtin et al. 2001; Thomas 2004) have been important in outlining the features of the Chesapeake ecosystem and in discussing the relationship between geography, environment, and human activity. The essays in Discovering the Chesapeake look at the geological heritage of the Chesapeake Bay, its climate, its ecosystem, and how humans have impacted it. Neither Curtin, Brush, Fisher and their fellow authors nor Thomas looked specifically at migration, although the essays in Discovering the Chesapeake, including contributions by historians such as Lorena S. Walsh, Warren R. Hofstra, Carville Earle, Ronald Hoffman, Anne Yentsch, and William Cronon, address the colonial environment, colonial Chesapeake forests, colonial agriculture, agrarian reform, and the ways humans interacted with the Chesapeake environment more generally. Cronon’s own contribution to the volume builds on his pathbreaking study Changes in the Land: Indians, Colonists, and the Ecology of New England (Cronon 1983). Migration is implicit in these works and also plays a role in such studies as those by Edmund Morgan, Lois Green Carr, Jean and J. Elliott Russo, Debra Meyers and Melanie Perrault, and others, although usually as a background factor rather than as a primary focus (Morgan 1975; Tate and Ammerman 1979; Carr et al. 1988, 1991; Russo and Russo 2012; Meyers 1997, 2003; Meyers and Perreault 2006, 2014; Land 1981; Land et al. 1977; Billings et al. 1986; Rutman and Rutman 1984a, 1984b). Although this study focuses primarily on Maryland, in addition to works just cited, other studies of seventeenth-century Virginia, and the colonial Chesapeake more generally, have also been relevant in terms of the political, social, and economic configuration of the Chesapeake region (Billings 1991, 2004, 2007, 2010, 2011, 2021; Billings and Tarter 2017; Heinemann et al. 2007; Parent 2003, 2025).

Within the field of early American history, David Hackett Fischer’s Albion’s Seed: Four British Folkways in America (Fischer 1989) synthesized the vast historiography of early America to argue that colonists transplanted four distinctive regional British folkways to different regions of early America. Settlers from East Anglia transplanted one regional culture to New England. Settlers from southeastern England transplanted a different regional culture to the Chesapeake. Settlers from the western Midlands transplanted a third regional culture to Pennsylvania. And settlers from the British borderlands, including northern Ireland, Scotland, and northern England, transplanted a fourth, and very different, regional culture to the Backcountry region spanning the Appalachian Mountains from western New Hampshire all the way down to what became northern Alabama, Georgia, Tennessee, and Kentucky, as well as the western parts of the original colonies. Fischer’s approach blended history and anthropology by focusing on the importance of folkways that shaped the fabric of daily life, including naming patterns, cooking patterns, clothing and dress, religious beliefs, political beliefs, attitudes to the elderly, childrearing customs, architectural patterns. These he attributed to the persistence of ancient regional influences deriving from the ancient kingdoms that came together to form England and, eventually, modern Ireland, Scotland, and Wales, fused together into a United Kingdom through acts in 1284, 1536, 1707, and 1801. Additionally, Fischer incorporated insights from demography throughout his overall approach. Beyond qualitative cultural analysis, he grounded the work in statistical analysis informed by the methodology of New Social History in the 1970s and 1980s (Fischer 1989). In the thirty-five years since its publication, Fischer’s work has drawn criticism from many fronts, including its skewed portrayal of the British borderlands region and its failure to incorporate non-British cultures into the story of early American life. Additionally, the work altogether failed to incorporate the considerable influence of African American peoples on regional development, particularly in the Chesapeake colonies where they comprised a significant component of the population. But the theoretical framework Fischer constructed, blending history and anthropology, remains a powerful analytical construct.

Fischer’s work represented a vast synthesis of the historiography of early America that has added to the work’s own persistence within historiography. The New Social historians of the 1970s and 1980s had produced scores of county and community studies important methodologically as well as for what they revealed about the fabric of local life in places like Salem, Massachusetts (Boyer and Nissenbaum 1974), Dedham, Massachusetts (Lockridge 1970), the Eastern Shore (Breen and Innes [1980] 2005), and the seventeenth century Chesapeake (Morgan 1975). In their study, Boyer and Nissenbaum revealed the socio-economic tensions that could fracture local society at Salem, and at Dedham Kenneth Lockridge showed how geography, climate, longevity, and inheritance customs could shape generational tensions within a local community. Breen and Innis examined how a period of socio-cultural fluidity that included intermarriage, collaboration, and exchange between peoples of African and English descent would later give way to a more restrictive, hegemonic society that disenfranchised many of those same families. Edmund Morgan chronicled the larger transformation of Virginia, and to an extent the Chesapeake World more generally, from a society dependent on vast numbers of white indentured servants into a hegemonic, plantation-based, slave-holding society (Morgan 1975).

Numerous state and local studies both shaped and were shaped by these and other similar studies. Aubrey Land (Land 1981) provided a narrative history of Maryland’s colonial development that incorporated recent scholarship, as did Billings et al. for colonial Virginia (Billings et al. 1986). Ongoing work by these authors and other scholars like Emory Evans, Kathleen Brown, James Horne, James Axtell, Frederic Gleach, and many others in the 1990s and early 2000s further shaped the understanding of life in the colonial Tidewater region (Brown 1996; Evans 2009; Axtell 1985, 1988, 1992, 1997, 2000; Horn 1995; Gleach 2000). Considering Maryland in particular, the works of the “Hall of Records Gang”—including Lorena S. Walsh, Lois Green Carr, Cary Carson, and others—refined the understanding of life not only in colonial Maryland but throughout the Chesapeake more generally. Rich primary source analysis based on land patents, deeds, probate inventories, wills, court minutes, and documents located abroad in archives in the U.K. grounded these works. In the past twenty years, the widespread availability of primary source material digitized by the Maryland Archives (formerly the Maryland Hall of Records), the Library of Virginia (formerly the Virginia State Library and Archives), Familysearch.org, Ancestry.com, and entities based in the United Kingdom, such as The National Archives, Findmypast.org, and the Society of Genealogists, have transformed the ability to research daily life in the Chesapeake as well as the history of the early colonists who settled there. In particular, by expanding the original print series Archives of Maryland to Archives of Maryland Online, the Maryland Archives has made available 865 digitized volumes of transcribed and indexed records relating to Maryland’s history. Beyond this, they also provide access to scores of other digitized, not-yet-transcribed materials, including deeds, probate records, land grant records, and rent rolls. Additionally, Maryland Land Records, an online database operated through the Maryland Archives, offers digitized copies of the land records from Maryland’s twenty-four county clerks, including the majority of surviving recorded colonial deeds (Archives of Maryland Online 1999–2025).

Adding to this, researchers on the Eastern Shore have worked extensively to preserve and make accessible records pertaining to the history of that region. Clayton Torrence, Susie M. Ames, and Ralph T. Whitelaw produced studies of Somerset, Accomack, and Northampton Counties still widely used today (Torrence 1935; Ames 1954, 1973; Whitelaw 1951). J. E. Russo’s published Somerset County tax records (Russo 1992), in addition to the digitized material now available through the Maryland Archives, provides a wealth of demographic data about early residents of the colonial Eastern Shore. More recent works by Howard Mackey and Marlene Groves (Mackey et al. 1999–2006) have also produced thorough transcriptions of early Eastern Shore records that go beyond the earlier studies of Ames and Whitelaw. Additionally, local history groups throughout the Eastern Shore have worked diligently to gather and preserve material relating to the region’s past. In recent years, this has taken the form of online websites such as M.K. Miles’s database, MilesFiles 23.0 (Miles 2025), made available through the Eastern Shore Regional Library System’s Eastern Shore of Virginia Heritage Center, and Marshall’s Early Colonial Settlers of Southern Maryland and Virginia’s Northern Neck Counties (Marshall 2025). While not academic in nature, user contributed websites like Genealogy and History of the Eastern Shore (GHOTES 2025) and the USGenWeb Project county sites and USGenWeb Archives sites for Eastern Shore counties (MdGenWeb 2025; USGenWeb 2025) contain maps, records indexes, digital images, and document transcriptions that can serve as a basis for further research. Additionally, the work of the Edward H. Nabb Research Center for Delmarva History and Culture at Salisbury University has centralized research materials for the Eastern Shore and produced a number of publications and digital collections (Nabb 2025). These include the works of former director G. Ray Thompson about early Somerset Co., MD, probate inventories, among them the excellent volume co-authored with Jennifer Lovellette about women’s probate inventories between 1677 and 1726 (Lovellette and Thompson 1996; Thompson 1997, 2004). The Nabb Research Center also sponsored a series of helpful publications by Wilmer O. Lankford (Lankford 1990–2002) that provide a concise directory of early Somerset County settlers. Additionally, works by Robert W. Barnes, Edward F. Wright, Harry Peden, Vernon Skinner, and others (Barnes et al. 1996–2025; Moxey and Skinner 1995; Skinner 1988–1991, 1992–1994, 2004–2011, 2015, 2016a, 2016b) have produced a host of reliable transcribed and indexed seventeenth- and eighteenth-century documents. Skinner’s extensive work with Maryland probate administrations and inventories as well as with colonial debt books (Skinner 1988–1991, 1992–1994, 2004–2011, 2015, 2016a, 2016b; Moxey and Skinner 1995) provides useful information about decedents, the nature and value of their possessions, and family and community connections. The contributions of Wright, Peden, Barnes, and others to the Colonial Families of the Eastern Shore of Maryland (Barnes et al. 1996–2025) provide helpful background context concerning many colonial settlers. Along with Wright’s own transcriptions of many Eastern Shore records, they have greatly amplified the arsenal of reliable research materials accessible to those interested in the Eastern Shore of Maryland and Virginia (Wright 1982, 1986). The published volumes of Eastern Shore genealogies by Wright, Barnes, Peden, and others (Barnes et al. 1996–2025) are reliable overall and provide extensive materials to serve as a groundwork for other researchers, as do essays on Eastern Shore families published in leading genealogical periodicals such as The American Genealogist (Ljungstedt 1936–1937; Russell 1980, 1985, 1990, 2001; Hansen 1989, 1991; Knight 2017; Hatcher 2021).

Over the past two decades, as a result of these efforts, the amount of transcribed and digitized primary source research materials relating to colonial Maryland and Virginia has increased greatly. Many of the secondary works, including published family histories, have tended to focus on European-American families. This is partly due to limitations in the surviving records, which these past individuals created to preserve and protect their own property and power. It is also partly due to a failure of earlier researchers to seriously study the Native American groups residing in the region when Europeans arrived or the people of African descent who lived there from the earliest settlements onward. Over the past decades, this has changed significantly. Research by Helen Rountree, Thomas Davidson, and others has enriched the study of Native American society on the Eastern Shore (Rountree and Davidson 1997; Rountree and Turner 2002; Rountree 1990, 1992, 1993, 2005). Rountree and Davidson employ archaeological, historical, and ecological research to examine the Native American peoples of the Eastern Shore. Through a chronological approach that traces Native peoples from pre-contact through the late eighteenth and early nineteenth centuries, Rountree and Davidson show that significant diversity existed among the Native American societies on the Eastern Shore and argue that these were distinct peoples with unique languages, identities, and customs. Rountree, an expert on the Powhatan Confederacy, and Davidson show that the Native peoples of the Eastern Shore were not simple extensions of the Powhatan Confederacy but, instead, local groupings with their own political structures and societal customs. Their work intersects with scholarship by James Axtell, a pioneer in ethnohistorical research whose scholarship combined history, anthropology, and ethnohistory (Axtell 1985, 1988). Axtell looked at Native-European interactions across colonial American society, however, while Rountree focuses primarily on the Algonquian-speaking peoples of colonial Virginia and the Powhatan Confederacy in particular (Axtell 1985, 1988, 1992, 1997, 2000; Rountree 1990, 1992, 1993, 2005; Rountree and Turner 2002).

Work by Thomas Davidson and Paul Heinegg on African American families has expanded understanding of the free black population on the Eastern Shore during the colonial period (Davidson 1991; Heinegg 2000). Davidson’s contributions to the volume coauthored with Rountree (Rountree and Davidson 1997) draw from his expertise in this subject. Paul Heinegg’s research documents many African American and mixed-race families of African American descent on the Eastern Shore across several generations. Like Heinegg, Davidson also examines the intersections between the free black community and Native Americans and European American settlers. But, while Heinegg’s work is primarily genealogical in nature, Davidson also examines the social, legal, and economic challenges free African Americans faced.

Following the publication of Morgan’s American Slavery, American Freedom (Morgan 1975), Breen and Innis (Breen and Innes [1980] 2005) first brought the complex nature of racial relations on the Eastern Shore to the attention of historians. Later, Ira Berlin examined what he termed “Atlantic Creoles.” As Berlin defined them, Atlantic Creoles utilized “linguistic dexterity, cultural plasticity, and social agility” to carve out a unique space for them and themselves in colonial society (Berlin 1996, 1998; Landers 2011). This group included Eastern Shore figures also discussed by Breen and Innis, such as Emmanuel Driggers and Anthony Johnson. Of African birth or descent, they and other similar individuals often owned property and lived as free people, although their descendants sometimes became enslaved. Heinegg’s work has expanded the focus on many of these individuals and their families across multiple generations, often documenting family relations between people of African descent, people of Native American descent, and people of European descent on the Eastern Shore (Heinegg 2000).

Importantly, building off earlier work by scholars like Moses Finley and Orlando Patterson, Berlin in his generational and regional analysis of American slavery articulated the distinction between slave societies, those where slavery dominated as the labor system and played a central role in the economic and social systems, and societies with slaves, those where slavery existed as one of multiple labor systems and played a less foundational role in social organization than in slave societies (Berlin 1998, 2003; Finley 1980; Patterson 1982). Anne Yentsch and J. E. Russo have examined the development of slavery on the Eastern Shore, which included both large plantations like those of Edward Lloyd in Talbot County and many individuals who owned few or no slaves (Yentsch 1994; Russo 2004). Although slavery was critical, colonial Dorchester was a society with slaves. For most of the seventeenth-century, indentured servitude played a key role in the local economy. Beginning in the middle seventeenth-century, the numbers of enslaved people began to increase in the region, but a considerable and growing free African American population existed alongside large numbers of European American families that owned little or no land and no slaves. Some planters owned many slaves. But Dorchester County and the Eastern Shore more generally had a lower slave population than in the Tidewater regions of Virginia, and the local economy included mixed agriculture and small farming, timber production and shipbuilding, and a significant intercolonial trading network with links to other colonies (Berlin 1998, 2003; Yentsch 1994; Russo 2004; Clemens 1975, 1980; Moser 2011; Ford 2006; Jones 1925; Mowbray 1979).

The works of several other scholars have helped frame European-American society on the colonial Eastern Shore in ways that have influenced this essay. In contrast to earlier studies that stressed the chaotic nature of political and social leadership in the colonial Chesapeake, James Perry’s The Formation of a Society on Virginia’s Eastern Shore, 1615–1665 (Perry 1990) argued that a more stable, permanent society took shape on the eastern shore early on than had previously been recognized within Virginia historiography. Perry’s approach countered a previous understanding of Chesapeake society that stressed the abrupt cleavages in leadership and authority caused by the early deaths of so many colonists. John Rushton Pagan took this analysis further through his in-depth study of Accomack and Northampton County, Virginia county court records. This appeared first in his 1996 Oxford D.Phil. thesis, “Law and Society in Restoration Virginia” (Pagan 1996) and later through the much shorter volume derived from that earlier work, Anne Orthwood’s Bastard: Sex and Law in Early Virginia (Pagan 2003). Pagan’s work shed light on how colonists transplanted English culture, including thinking about law and law’s relationship to society, to the Chesapeake and transformed it there. In the course, Pagan’s meticulous reconstruction of society in Accomack and Northampton Counties built on Perry’s earlier work and carried the analysis into the later seventeenth century. Together, Perry and Pagan show that a core leadership group took shape early on the Eastern Shore. Despite high mortality and the fact that many leaders had come from outside the traditional ruling groups in England, an evolving leadership group formed whose members, through birth, marriage, remarriage, or family relationships, could often trace their origins to the first or second decade of settlement on the Eastern Shore. And, although legal processes differed from those in England, they protected property, promoted social cohesion, and provided a resource that individuals like Jasper Orthwood, the illegitimate son of an indentured servant, could utilize for their own benefit.

The essay that follows addresses Chesapeake Bay geography and places the Eastern Shore within it before reviewing the four major migration routes into Dorchester. It asks how distinct migration patterns shaped the social, religious, and cultural development of Dorchester County in particular and the Eastern Shore more generally during the colonial period. Through the lens of migration history, it also contributes to study of Eastern Shore society developed by Perry and Pagan by shifting attention northward into southern Maryland and looking at the migration routes that brought settlers there, including individuals who went on to become members of Dorchester’s colonial leadership group. Migration brought some members of other regional elites into Dorchester County. In this fluid society, newcomers, including some from outside the traditional leadership group, were able to achieve social, political, and economic success. They did so at a price, however, that included the exploitation of slaves and white indentured servants as well as the devastation of Native American societies. A concluding section discusses migration, culture, and outmigration from Dorchester. Extensive primary sources available at the county level for the Eastern Shore as well as colony-level land and probate records held by the Maryland Archives greatly facilitated this research. My approach to Chesapeake society on the Eastern Shore has been influenced by the work of Perry and Pagan (Perry 1990; Pagan 1996, 2003) and draws in a more general way from an understanding of Chesapeake society developed through the work of Carr, Russo, Curtin, Meyers, Perreault, and others (Carr et al. 1988; Russo and Russo 2012; Curtin et al. 2001; Meyers and Perreault 2006, 2014). Ravenstein and Catapano (Ravenstein 1876, 1885, 1889; Catapano 2025) shape the theoretical framework regarding the causes, methods, and consequences of migration. Work by Fischer and Bailyn on migration and culture in early America provide an overall context for understanding the Chesapeake, and the Eastern Shore in particular, within the British Atlantic World of the early modern period (Fischer 1989; Bailyn 1988, 2005, 2012; Bailyn and DeWolfe 1986). Throughout, the approach to microhistory articulated so eloquently by John Demos and Darrett and Anita Rutman has served as a methodological model (Demos 1982, 1996, 2000, 2020; Rabb and Rotberg 1973; Rutman and Rutman 1984a, 1984b).

Regarding Dorchester County, its early history, and its people, the works of Elias Jones, Calvin and Mary Mowbray, and James A. McAllister have been indispensable (Jones 1925; Mowbray 1984; Mowbray and Mowbray 1992; McAllister 1962, 2002). Elias Jones wrote an early Dorchester County history that covered the county’s social, economic, and political development. Although not an academic monograph, it provided helpful context on many facets of early Dorchester society. Additionally, publications by Calvin and Mary Mowbray and James McAllister provided critical primary source material that informed this study. Although they attempted no quantification or analysis, Mowbray and Mowbray systematically abstracted early Dorchester land grants in two volumes spanning nearly 400 pages. These abstracts provide key information about the dates of land grants, the prior residences of many migrants, and the locations of the grants themselves. Calvin Mowbray also produced genealogies of many of these families that included abstracts of wills and other legal documents. McAllister’s abstracts of early Dorchester deeds, which span the entire colonial period, document the arrival dates and prior residences of many other early Dorchester settlers not among the original grantees. While some dates remain approximate, together these primary source abstracts provide the core data that informs this study. Interested readers may thus refer to them for further details about the individuals discussed here, their backgrounds and origins, and their land dealings in colonial Dorchester County.

3. Geography

The distinctive Chesapeake geography shaped the region’s settlement and later migration within it after the first settlements had become established locales. The multiple rivers flowing into the Chesapeake Bay provided large interior waterways, and those within Virginia were navigable to the fall line, which marks the boundary between the coastal Tidewater region and the Piedmont. Migration into the region came via the Atlantic Ocean as part of England’s vast commercial network. Once in the bay, ships traversed the coastal waterways, trading with local plantations. In both Virginia and Maryland, a plantation-based economy developed, and major towns were few and far between (Thomas 2004; Carr et al. 1988; Curtin et al. 2001; Billings 2007).

An understanding of the region’s geography is critical to understanding migration within the Chesapeake Bay region. West to east and south to north migration routes seem counterintuitive to those who study the settlement and development of the lower South and Midwest, where most migration proceeded in a southwesterly direction. The first English settlers sought sheltered locations that afforded protection from weather and the elements, from hostile native Americans, and from other Europeans who might venture into the area. As settlements grew, colonists moved outward in search of land and resources, usually following the same riverways further inland (Billings 2007; Rutman and Rutman 1984b; Billings et al. 1986).

Even within the locales, the riverways shaped local settlement patterns and regional economy. Although he argues for a dynamic system that responded to economic, social, and demographic changes, historical geographer Carville Earle has stressed the primary importance of the ability to navigate riverways, proximity to the Chesapeake Bay, and local soil fertility in determining Chesapeake settlement patterns (Earle 1975, 1979). Colonists settled near the major rivers, and the marshy, riverine geography of much of the area meant that a society formed that included small scale mixed farming, shipbuilding, and trade as well as plantation-based agriculture. Settlement of the interior moved inward. Large land grants meant that most of eastern Virginia, which had opened for settlement in 1607, nearly thirty years before colonists arrived at St. Mary’s, filled quickly after tobacco cultivation took hold. Even before that, the formation of local hundreds and plantation settlements indicated that colonists quickly moved up the waterways towards the fall line. Native settlements limited where colonists could move, and, in 1622 and 1644, native revolts attempted to repel the white Virginians altogether. (Billings et al. 1986; Billings 2007; Noël Hume 1991; Clemens 1975, 1980; Ford 2006; Moser 2011).

On the Eastern Shore, the narrow isthmus of land extending into the bay and originally known as the “Kingdom of Accomac” attracted colonists. Settlers arrived in the second decade of British colonization, and James Perry has argued that a politically and socially coherent society began to form on the Eastern Shore at an early date. Accomac County, formed in 1634, became Northampton County in 1642. Later, Northampton divided into two counties, with the newer county formed from the northern portion of it named Accomack. The area north of Accomack lay in Maryland, and native peoples lived throughout the region. When British settlers arrived in the middle seventeenth century, they moved inland from the Atlantic and interior Chesapeake Bay coasts. The lower peninsula is, at its widest point, only about twelve miles wide. Further north, at its broadest point, in the area between Salisbury, Maryland, in present-day Wicomico County,1 and Cambridge in Dorchester County, the peninsula is sixty to seventy miles across. (Thomas 2004; Curtin et al. 2001; Perry 1990; Pagan 1996; Torrence 1935).

European-American migrants to colonial Dorchester followed four main routes. One was a north to south migration route that brought settlers into the county from New York, Pennsylvania, Delaware, and neighboring Talbot County, Maryland. Another was an east to west migration route that brought some settlers into present-day Dorchester County from eastern Maryland and what later became southern Delaware. The distance from the present-day Dorchester boundary to the Atlantic coast is only about thirty-five miles wide, which limited the potential for the traditional east to west migration route. Some migrants traveled into Dorchester from abroad, however, although some of these may have entered Dorchester from the Chesapeake Bay’s interior coastline rather than from the peninsula’s Atlantic coast (Mowbray 1984; Mowbray and Mowbray 1992; McAllister 2002).

The north to south and east to west migration routes were more typical of U.S. migration history, but added to these were two more patterns. One was a west to east migration route that brought settlers from the counties on the west side of the Patuxent River into colonial Dorchester. Another was a south to north migration route that brought settlers from as far as Isle of Wight and Nansemond Counties south of the James River more than one-hundred and fifty miles northward into Dorchester County. In some cases, the two routes intersected, with southern migrants from Virginia traveling first to the west side of the Patuxent River and living there for a number of years before crossing the Patuxent River and Chesapeake Bay into Dorchester County (Catapano 2025; Mowbray 1984; Mowbray and Mowbray 1992; McAllister 2002).

All of these migrants functioned within an Atlantic migratory culture (Bailyn and DeWolfe 1986; Bailyn 1988, 2005; Games 1999). Many of the early Dorchester settlers had been born across the Atlantic Ocean, in England, Wales, Scotland, Ireland, or France. For them, settlement in Dorchester was another phase, often the ultimate one, of a journey that had first begun with migration from rural villages into larger urban areas like London, Bristol, Liverpool, Dublin, or Glasgow (Bailyn and DeWolfe 1986; Bailyn 1988; Games 1999). While the analysis here focuses on four separate patterns, in many cases those patterns became interwoven and overlapping. As part of process of step migration driven by social, cultural, economic, and religious factors, these migrants first settled in one region before moving to another. They existed within an Atlantic framework shaped by ongoing social, cultural, political, and economic change across the seventeenth century, including commercial and religious networks that linked the Chesapeake with New England, the Caribbean, the British Isles, and continental Europe (Hatfield 2004).

Two examples illustrate this point. The first is the case of Richard Preston, born about 1619 in England. Like others, Preston would most likely have traveled first to a larger English city, where he probably resided for a period of time. He first appeared in Virginia south of the James River in Norfolk County in 1644. As part of the Puritan community in Norfolk County, following the execution of Charles I in 1649, he moved with his family to Calvert County, Maryland. William Stone, a wealthy Puritan merchant who had settled in Virginia before 1622, became Maryland’s governor in 1648. Stone welcomed fellow Puritans into the Maryland colony, and many Virginia Puritans headed north. Preston spent a decade in Calvert County but established himself in Dorchester, which he represented three times in the lower house of the Maryland Assembly, by 1663 (Troth 1892). A case that highlights the considerable cultural variation within early Dorchester society is that of Antoine LeCompte. LeCompte had been born in “Callis” in France but settled in London during the 1650s. LeCompte may have been affiliated with the Huguenot community that had established itself in the Spitalfields area of eastern London in the seventeenth century. He lived in London during the 1650s and married at St. Helen’s, Bishopsgate, in 1661 to “Esther Dottando of Deepe,” a French woman also living in London.2 Their likely places of origin were Calais and Dieppe, French coastal towns about eighty miles apart and a similar distance from London itself. The LeComptes first settled in Calvert County on Maryland’s western shore. After a few years, they returned to France. But by 1669, they had relocated to Dorchester County on the Eastern Shore. They spent the rest of their lives there and founded a family that figured prominently in the region’s history (Culver 1917).

Although these migrants existed within a dynamic Atlantic framework that Bernard Bailyn characterized as “worlds in motion” (Bailyn 1988), they lived on a simpler scale with each individual decision influencing another. Few, if any, began their journeys with initial goal of settling in Dorchester County. Instead, they followed varied trajectories, often as part of chain movements of related families, from one location to another. The following pages examine each of the four regional migration routes and how and why they brought different streams of settlers to Maryland’s Eastern Shore.

4. Migration from the North

Settlers began patenting lands in Dorchester County in the 1650s, more than a decade before the formation of Dorchester County as a governmental entity in the late 1660s (Mowbray 1984). They first patented tracts along the Chesapeake Bay shoreline, including the numerous islands located off its coast, and along large interior waterways. Many initial grants were small, but later ones included single tracts of more than two thousand acres. At the time these Europeans began arriving in Dorchester, Native peoples still lived in the area. Although gradual, movement into Dorchester began a process of spatial construction that would transform Native lands into farms, plantations, and commercial centers. Large towns and cities were few in the Chesapeake due to its riverine geography and plantation-based agriculture that meant ships could sail far inland. Cambridge, a small town founded in 1686 that originally functioned as a plantation port, became the county seat. Grants to and settlement by European colonists not only began a process of spatial construction that would transform the world of Native Americans living on the Eastern Shore, but it also initiated a process of territorialization and settler colonialism that aimed to define boundaries and assert sovereignty over the natural landscape. Over time, this led to the reduction of Native peoples and their influence regionally even as it created new spatial relationships and experiences among the settler population. Importantly, while the Native population in Dorchester declined, it was not eliminated, a point discussed further in the concluding sections. As part of the process of remaking the Eastern Shore’s landscape, European settlement pushed Natives to the interior. Treaties afforded them some protection, and lands reserved for them in northeastern Dorchester provided a literal “middle ground” from which the Natives interacted with the local populations in Dorchester, Somerset, and Talbot Counties. While the pages that follow focus largely on the diverse groups of European settlers who arrived in early Dorchester, the routes they took, and their motivations for migration, it is essential to recognize that they did not settle in an unpopulated land or remake a wilderness. Opportunity for them meant not only a lack of the same for Native populations in the region, which had already faced encroachments from Swedish and Dutch settlers to the north, but also a purposeful intent to deprive Native peoples of their lands and cultural autonomy (Cronon 1991; White 1991, 2010; Branch and Stockbruegger 2023; Wolfe 2006; Veracini 2024).

Settlers arrived in Dorchester simultaneously from the north, east, west, and south. For analytical purposes, however, the article examines these migration streams separately. One important and culturally distinctive migration route into colonial Dorchester County came from the north. This included migration from northern colonies into Dorchester by way of Delaware as well as migration from more northerly parts of eastern Maryland into Dorchester. Christopher Browne’s 1685 map, A New Map of Virginia, Maryland, and the Improved Parts of Pennsylvania & New Jersey, showed Dorchester at that time, approximately thirty years after the initial settlements in the area. Development centered along the Chesapeake Bay shore and the riverways that flowed into the interior, and a long swathe of land undeveloped by and uninhabited by Europeans stretched to the north and east. In present-day Delaware, settlement had proceeded primarily into the upper reaches of the Delaware Bay, a coastline shared on the west by present-day Kent County, Delaware, and on the east by the New Jersey shore and the small islands contained there (Browne 1685).

Figure 3 and Figure 4. Excerpts from Christopher Browne’s 1685 “New Map of Virginia, Maryland, and the Improved Parts of Pennsylvania,” showing Dorchester County and the surrounding Eastern Shore. Source: (Browne 1685).

A key component of this north to south migration was that it included not only British migrants from outside the predominant settlement patterns within Fischer’s Chesapeake paradigm but also non-British migrants whom Fischer fails to consider altogether. For many of these migrants, a desire to practice their religious faiths freely with other fellow believers, a factor that played little role in Ravenstein’s analysis (Ravenstein 1876, 1885, 1889), seems to have been a strong motivation to migrate. The case of John Richardson and his family provides an example of migration from this more northerly region through Delaware and then into Dorchester. Richardson seems originally to have settled in New Netherlands. He was mentioned in depositions between 1676 and 1680 as a resident of Dorchester County and may have been living there by 1672.3 Prior to coming to Dorchester, he had lived at Whorekill in present-day Kent County, Delaware, a settlement dating from 1642 and originally part of the region’s Dutch and Swedish foundation, when it was called Hoeren-kil or Hoere-kil. The region fell to the English in 1664, and Kent County was formed in 1681. Richardson may have been Dutch, possibly originally named Ricords or Rickords, although he may also have been of English background. Certainly, his name appears in both Maryland and Delaware on occasion as John Richards, but from the 1670s onwards, after taking up residence in Maryland, the form Richardson seems to have become standard (Turner 1989; Cohen 2004; Standing 1982).

While it is not clear whether Richardson was himself Dutch, other early Dorchester residents were of Dutch origin. The case of Jacob Loockerman offers an example. Loockerman, the only child of Govert Loockerman and Marritje Jans, was born in New Amsterdam in 1652. He had come to Maryland by 1678, when he married a daughter of Irishman Nicholas Keiting, who had settled in Maryland by about 1645 (Marshall 2025; Mowbray 1984). Loockerman’s wife Helena exemplified the ethnic and religious diversity of the region as well as the tendency of settlers of diverse backgrounds to mix together. She had first married Bryan O’Daly, another Irishman. Following O’Daly’s death in 1675, she married Loockerman (1652–1730) in 1678. It is unclear whether Keiting and O’Daly were themselves Catholic, but the 1674 will of Roger Shehee included bequests to Bryan O’Daly, Jr., and Constantine O’Keiffe as well as to the Roman Catholic Church. Sheehee seems to have remained in St. Mary’s County, but the Loockermans migrated from this religiously and ethnically mixed community—including associates named De La Roche and le Duc—into Dorchester County about 1679. It is possible that De La Roche or le Duc were Huguenots, followers of John Calvin, like the Loockermans, but it is also possible that they were Catholics like Roger Shehee seems to have been (Marshall 2025; Mowbray 1984; Barnes et al. 1996–2025).

Loockerman’s father Govert Loockerman of New Amsterdam was a prominent merchant there. Jacob Loockerman acquired land in Dorchester at the head of Hungar River in 1682, and he became a commissioner to erect ports and towns in 1683. In the coming years he held prominent political and military positions in Dorchester County and also became a delegate to the colonial Assembly that met in St. Mary’s. Loockerman’s family became a leading one in Dorchester and surrounding counties whose influence lasted throughout the colonial period (Mowbray 1984). Along with economic opportunity, the relative religious freedom in the colony may have influenced Loockerman’s decision to move south into Maryland. Like the English Puritans whom Governor Stone welcomed in 1649, the Dutch settlers of New Amsterdam followed the teachings of John Calvin. April Hatfield has examined the religious and economic networks that tied together Puritan families like the Allertons of Massachusetts and Virginia’s Northern Neck and Dutch ones like the Varletts, Hacks, and Hermans that moved from New Amsterdam to Accomack Co., VA, in the 1650s. These families remained after the Restoration, and newly settled Dorchester offered not only economic opportunities but a place of relative religious freedom with access to fellow believers (Hatfield 2004).

In addition to families like the Richardsons and Loockermans that came from further afield, many migrants into northern Dorchester came south from neighboring Talbot County, formed prior to 1661 when a 12 February writ naming its sheriff first mentioned the county. Settlers had already been in the area for several years, and beginning in the 1660s they began to move south from Talbot into northern Dorchester. Many, although by no means all, were Quakers and had ties to the Third Haven Meeting, which met in Talbot County by 1676. Other families in the area included members of the Church of England, and a small Roman Catholic presence on the Eastern Shore led to a chapel of ease built at Doncaster in Talbot County as well as a chapel at Meekins’ Neck in Dorchester, where several local Catholic families from St. Mary’s settled in the 1660s. Still, Dorchester had a relatively small Catholic presence in comparison with other faiths, and a listing in 1706 noted that only seventy-nine Catholics lived in the county at that time (Jones 1925; Mowbray 1984; Third Haven Monthly Meeting 1940).

As compared with the seventy-nine Catholic residents in 1706, the early Dorchester Quakers were at least as numerous and probably more so. The Carson, Edmondson, Fisher, Foster, Fowke, Kennerly, Parrott, Phillips, Pitt, Powell, Taylor, Willis, and Willson families of northern Dorchester are all known to have been Quakers prior to 1700 (Third Haven Monthly Meeting 1940). They appear in Quaker marriage records and minutes of the Third Haven Monthly meeting. Most had large families, and some held to the faith throughout the colonial period. Among colonial Catholic families in early Dorchester, the Tubmans are perhaps the best known, although some members of the Keene, Dean, Shenton, Staplefort, and Dunnock families were also Catholic (Jones 1925).

In addition to those mentioned above, many other early Dorchester settlers moved down out of Talbot County.

Table 1. This table contains the names of some early Dorchester settlers and landowners who settled first in Talbot County. The list is representative but not exhaustive. Dates reflect the occurrence of their name in deed, land grant, court, probate, or other documents and may have preceded their actual arrival in the colony. In some cases, dates have been estimated based on a subsequent appearance in such documents. (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025; Coldham 2002; Marshall 2025).

Name	Prior Residence	Date by Which in Dorchester
Richard Hughes	Talbot	1665
John Pritchett	Talbot	1679
Margary Price Pritchett	Talbot	1679
Daniel Maynadier	Talbot	1688
John Pope	Talbot	1682
Robert Roberts	Talbot	1682
Thomas Powell	Talbot	1665
Howell Powell	Talbot	1665
John Tench	Talbot	1679

summarizes names of some of them (Mowbray 1984; Mowbray and Mowbray 1992). Dates are from land grants, deeds, and other legal documents that may have preceded actual settlement by some years, but they do indicate interest in Dorchester and its lands. Once acquired, new landowners would have begun to develop their own lands for agricultural purposes or to subdivide and rent or sell them to others, a widespread practice.

Families like the Hughes and Powells lived in Dorchester by about the time the county was formed and had already been living in Talbot County for several years. Several of this group seem to have been of Welsh origin, including Richard Hughes, John Pritchett, Margary Price, Robert Roberts, and Thomas and Howell Powell, whom tradition holds descended from the Powell family of Castle Madoc in Powys, Wales (Mowbray 1984). Howell Powell and his family affiliated with the Quaker faith, as did other Welsh families like the Morris, Lewis, and Morgan families. In some cases, former Puritans also adopted the Quaker faith, as did Richard Preston’s descendants.

Dorchester County is less than one-hundred miles from the present boundary between Maryland and Pennsylvania and only 129 miles from Philadelphia, the epicenter of the Quaker world in colonial British north America. George Fox visited the Dorchester and Talbot County Quakers in 1672, and ties of kinship, marriage, and trade meant that Eastern Shore Quakers retained a distinctive identity throughout the colonial period. Over time, however, the Quaker presence shifted into Talbot County, where membership grew steadily, and the two satellite meetings in Dorchester disappeared by the middle of the eighteenth century (Carroll 1984). As Fox’s presence on the Eastern Shore in 1672 suggests, however, the Quaker migrants of early Dorchester functioned as part of an extended Atlantic network of fellow believers, much as did the early Dorchester Puritans.

Thus, migration from the north seems to have provided colonial Dorchester with distinctive elements that complicate the regional paradigms outlined by David Hackett Fischer in his classic work Albion’s Seed. By looking exclusively at settlers from Britain, Fischer failed to consider non-British groups and religious dissenters from Britain that moved into the Chesapeake from the middle colonies or the cultural variation within local societies throughout the larger Atlantic World. Early Dorchester settlers from the north included settlers of Dutch and possibly of Swedish origin as well as several families that had come from Wales, a group Fischer considers only as satellite peoples on the periphery of British migration. The majority of early Dorchester settlers did originate in Britain and the British borderlands region to the north, but early Dorchester society offered opportunities for non-British migrants to thrive. As Jack Greene, Alison Games, and other scholars have argued, the influence of dominant cultures was not always straightforward and hegemonic. Instead of assimilation into the dominant culture, identities tended to be negotiated. Cultural fluidity meant that settlers often spoke multiple languages and moved in and out of identities, combining elements of both rather than abandoning one in favor of another. As shown later, other migration routes into Dorchester brought French Protestants into the region. Early settlers may also have included a small number of Irish Catholics from across the bay in addition to Irish protestants who later came in large numbers. Linguistically, these first- and second-generation migrants would have spoken languages such as Dutch, Gaelic, or French in addition to whatever English they had acquired. Naming patterns and religious folkways would have differed from those of the British colonists as well (Fischer 1989; Greene 1993; Games 1999; Egerton et al. 2007).

Although some early migrants from the north were Anglican, many seem to have belonged to dissenting faiths that existed outside the framework of the Church of England. A more tolerant society, especially one where land and other economic resources offered the prospect of economic security and even wealth, may have drawn them southward into Dorchester. Over time, just as the number of Quakers in Dorchester dwindled, so too did the visibility of the Calvinists. The Loockermans offer an example of a family that retained elements of their prior identity even as they moved within Dorchester society. Over time, the Loockermans intermarried with other prominent Eastern Shore families, affiliated with the Church of England, and became part of the local governing elite. But the continuation of the given names Jacob, Govert, and Nicholas into the eighteenth-century highlighted their non-British background. Additionally, the family retained the surname Loockerman without Anglicizing it. The 1731 will of Jacob Loockerman, who bequeathed lands to his nephew Govert on the stipulation that they “pass in surname of Loockerman forever,” suggests that, even as the Loockermans may have adopted some behavioral patterns of wealthier English families, this was a deliberate action to retain the family’s non-British identity (Cotton and Henry 1904–1928).

Perhaps in relation to the growing presence of plantation-based agriculture and slave labor in the eighteenth-century, some of the Dorchester Quakers continued their migration to areas like Philadelphia, urban centers with much larger Quaker populations. An example is the family of Richard Preston, whose grandson Samuel, an influential Quaker merchant, became mayor of Philadelphia in 1711. Others left the faith when they intermarried with non-Quaker families. When they married out of unity, their monthly meetings disowned them. They may not have abandoned their beliefs entirely, but, like the Loockermans, through a process of cultural blending common throughout the Atlantic world, they began to take on blended identities, some of them also moving into the local political and social elite (Standing 1982; Mowbray 1984; Jones 1925; Mowbray and Mowbray 1992; Barnes et al. 1996–2025; Greene 1988, 1993).

5. Migration from the East

A significant and steady stream of migrations into Dorchester County in the seventeenth and eighteenth centuries moved westward into southern Dorchester from neighboring Somerset County. Nanticoke Hundred of Somerset County, located on the south side of the Nanticoke River, joined Dorchester County’s eastern boundary. At that time, the interior boundary was somewhat indeterminate but stretched about twenty-five miles from the mouth of the Nanticoke River northeasterly towards the Atlantic Coast. About half of it lay in what is today the state of Delaware, which then included northeastern Dorchester Co., MD, and northern Somerset Co., MD. (For a visual depiction, see: Somerset Hundreds in 1734 (Lyon 2004, http://www.mdgenweb.org/somerset/lyonmaps/1734hundreds.htm, accessed 1 August 2025). Colonists made attempts in the later seventeenth century to clarify the colonial boundaries, but not until the surveying of the Mason—Dixon line between 1763 and 1767 did the boundary become fixed (Danson 2001).

Settlers began to acquire land and move into Dorchester County from Somerset County at an early date. This route of migration never ceased during the colonial period. In colonial Somerset, Nanticoke Hundred, Wicomico Hundred, northern Pocomoke Hundred, northern Bogerternorton Hundred, and almost all of Baltimore Hundred lay east of Dorchester County (which originally included much of present-day Caroline County, formed in 1773), as did the unsettled region between Wicomico and Baltimore Hundreds not developed until the middle of the eighteenth-century. Baltimore Hundred’s eastern boundary spanned Somerset County’s entire Atlantic coastline (Jones 1925; Torrence 1935; Lyon 2004; Browne 1685).

The migration from Somerset County into Dorchester functioned, for most of these families, as one step in a longer chain that had begun elsewhere. Not settled until the 1660s, Somerset County had many early residents who moved north from the lower Eastern Shore counties of Virginia. Others came directly from England or Ireland as indentured laborers brought into the area in the 1660s, 1670s, and 1680s by merchant planters like William Stevens and David Browne, who patented thousands of acres of land there and sponsored laborers from England, Ireland, and Scotland to work on them. Stevens, one of the wealthiest residents of seventeenth-century Somerset, had been born in Buckinghamshire. David Browne, educated at the University of Glasgow, had several siblings who remained in Scotland. Although Stevens did not share the Presbyterian faith, both men had ties to Francis Makemie and other Presbyterian ministers in Ulster that facilitated the transportation of hundreds of indentured servants into the colony. Ulster Presbyterians belonged to what historians like Alison Games and Bernard Bailyn have termed “transatlantic communities,” particularly in the late seventeenth century, when a steady stream of migrants arrived in the Chesapeake. Experiences on both sides of the ocean shaped such communities, as did the migration experience itself, and they existed in the framework of other overlapping, often competing identities. Ulster Presbyterians faced political, economic, and religious challenges in the 1680s and 1690s, and many opted to leave Ulster for opportunities elsewhere. In addition to Stevens and Browne, ministers like Francis Makemie, Thomas Wilson, William Traile, and Samuel Davis functioned at the nexus of transatlantic networks that reached into local communities throughout Ulster and Lowland Scotland and connected them with the Eastern Shore and greater Atlantic World. Makemie visited the Caribbean, where many Irish servants had settled in the 1650s and 1660s, and lived for extended periods in the Chesapeake. He corresponded with Irish Presbyterians, New England Puritans like Cotton Mather, and political figures in a number of colonies about religious matters. William Traile and Thomas Wilson both preached in Ireland but had close ties to southwestern Scotland, where Traile had lived his early life. They traveled to the Chesapeake followed by members of their congregations. In Maryland and Virginia, they served Presbyterians already settled there as well as new converts from other denominations. Following Makemie’s arrival in Maryland in 1683, ongoing communication with Ulster Presbyterians led hundreds of migrants across the ocean over the next two decades and involved extended communities on both sides of the Atlantic. While some of the followers of Makemie and his fellow ministers paid their own way, many seem to have come as servants to work lands owned by Stevens, Browne, and others (Torrence 1935; Sherling 2015; Bailyn 2005; Games 2006). By the 1680s and 1690s, many of these servants had completed their indentures and moved into northern Somerset County, where they seem to have rented lands from Stevens, Browne, and men like them. From there, they began to cross the Nanticoke River into southeastern Dorchester County.

Given the direction of this migration stream, most residents of eastern Dorchester County had once lived in or had family and business connections to western Somerset County. Local ferries and bridges connected the two sides of the Nanticoke River, and settlers seem to have crossed routinely for business purposes, religious worship, family gatherings, and community events such as weddings, baptisms, and estate sales. Careful study of Somerset County tax lists suggests that migration back and forth between the two counties occurred frequently. Edward Wheatley, ancestor of the Wheatley family of eastern Dorchester County, began his life in Maryland as an indentured servant in Somerset County in the 1690s. He may have come from Baltimore Hundred near the Atlantic coast, but he eventually lived near the Nanticoke River in the western region of the county. Wheatley died early but left several young children. Dorchester County land and probate records show them intermittently in Dorchester County, where they primarily resided, and Nanticoke Hundred of Somerset County during the 1720s, 1730s, and 1740s. This illustrates the back-and-forth movement between eastern Dorchester and western Somerset, whose boundary—despite it being a substantial geographical divider—seems to have been porous in nature (Russo 1992; Barnes et al. 1996–2025; Jones 1925).

Many early Dorchester families had a background in Somerset County, and migrants continued to enter Dorchester from Somerset throughout the eighteenth century and beyond.

Table 2. Early Dorchester settlers who arrived from Somerset County. The list is representative but not exhaustive. Dates reflect the occurrence of the name in deed, land grant, court, probate, or other documents and may have preceded their actual arrival in the colony. In some cases, dates have been estimated based on a subsequent appearance in such documents. (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025; Coldham 2002; Marshall 2025).

Name	Prior Residence	Date by which in Dorchester
Elizabeth Woolford Ennalls	Somerset	1685
William Green	Somerset	1669
Sarah Denwood Hicks	Somerset	1680
Mary Woolford Hooper4	Somerset	1689
William Harper	Somerset	1710
Henry Lake	Somerset	1710
Sarah Woolford Loockerman	Somerset	1700
Milleson Marine/Mareen	Somerset	1670
Christopher Nutter	Somerset	1683
Solomon Turpin	Somerset	1700
Joseph Wheatley	Somerset	1735
William Wheatley	Somerset	1735
Thomas Wilson	Somerset	1700
James Woolford	Somerset	1698
Roger Woolford	Somerset	1704
Edward Wright	Somerset	1690

provides known examples who entered Dorchester County before 1735 (Mowbray 1984; Mowbray and Mowbray 1992).

The examples above illustrate different scenarios that brought families out of Somerset into Dorchester as well as the ongoing nature of the exchange with Somerset County. The first Roger Woolford married Mary Denwood in Somerset. They reared a large family of children there. Roger died in 1702, and his adult children—born between 1663 and 1683—all began moving into southern Dorchester County near the turn of the eighteenth century. James Woolford lived there by 1698, and Roger Woolford, Jr., first acquired land there in 1704. Several daughters married men from Dorchester and settled there. These ties united the Denwood, Woolford, Ennalls, Hicks, Hooper, and Lockerman families into a prominent group that included large property-owners, county officials, military leaders, interpreters and negotiators with Native peoples, and members of the colonial Assembly. They ultimately became one of Dorchester’s most powerful political dynasties in the later colonial period (Barnes et al. 1996–2025).

At the opposite end of the spectrum were William Wheatley and his brother Joseph Wheatley, sons of the indentured servant Edward Wheatley of Somerset County. The brothers appeared in Somerset County tax records in the early 1730s but had moved across the Nanticoke River into Dorchester County by the middle 1730s. They eventually acquired small tracts of land and established self-sufficient families, although neither brother became wealthy. Dorchester and Somerset County records suggest that while they lived and worked primarily in Dorchester, they had close business and family ties in western Somerset. Joseph Wheatley, for instance, married a daughter of James Phillips, a mariner, who appeared frequently in western Somerset. Phillips himself had moved into Somerset County from Dorchester, where he married the daughter of John Kirk, founder of Cambridge. Her grandfather John Rawlins, an early Dorchester resident, had relocated from the south side of the Patuxent River. The son of an indentured servant, Wheatley never became wealthy, but he had ties through marriage to several prominent Dorchester families. Wheatley died in Dorchester, and his descendants remained there into the nineteenth century. Although Wheatley spent his final years in Dorchester, a series of back-and-forth migrations into and out of Dorchester County from Somerset that complicate Ravenstein’s theory of step migration punctuated his life. His case also shows how a relative newcomer of lower socio-economic status could integrate into an older and better-established family network. Unlike cases where such events facilitated economic advancement, there seems to have been little material benefit for Wheatley or his children. In contrast to Wheatley, however, families like the Woolfords were able to use alliances with the Dorchester establishment for economic and social gain (Ravenstein 1885, 1889; Russo 1992; Barnes et al. 1996–2025; Archives of Maryland Online 1999–2025).

Linked with migration from Somerset County were two other migration paths that brought settlers into Dorchester. One was an even more westerly migration that drew immigrants across the Atlantic Ocean from England, Ireland, France, and other locations to Dorchester County. Some of these had settled in Somerset County first. Others may have arrived directly into Dorchester County, perhaps traveling into the Chesapeake Bay by boat and arriving in Dorchester from the eastern side of the bay (Mowbray and Mowbray 1992; Mowbray 1984; Barnes et al. 1996–2025). Their journey had begun thousands of miles away, and arrival in Dorchester represented another step in a series of migrations.

It is often difficult to document the origins of colonial colonists since detailed ship manifests do not exist. Many early Dorchester colonists were born in England, Wales, Scotland, Ireland, or western Europe, but in most cases their exact points of origin are unknown. Enough documents survive, however, to identify the places of origin of some Dorchester settlers who arrived from abroad. In addition to the Welsh colonists in northern Dorchester already discussed, this group included settlers of varied origin (Mowbray 1984; Barnes et al. 1996–2025).

Several early Dorchester settlers are known to have come from England. Early Dorchester landowners Raymond Staplefort and George Thompson, who married Staplefort’s sister, came from England. They had interests in Virginia and Calvert County as well as in Dorchester, where they appeared in legal records during the 1670s. Staplefort’s descendants, including members of the Tubman family, settled permanently in Dorchester. Nicholas and Margaret Goldsborough hailed from Dorsetshire in England, and the Keene brothers who settled in Dorchester were natives of Surrey, near London. Likewise, Thomas Hicks, who married Sarah Denwood, sister of Mary (Denwood) Woolford, was born in England about 1656, probably in Whitehaven, Cumberland, in the far north (Downing 1916; Mowbray 1984; Marshall 2025; Barnes et al. 1996–2025).

Patrick Mullikane of Dorchester came from Ireland. William Geoghagan, another Irishman, traveled from Dublin. John Henry, an early Presbyterian minister, settled first in Somerset County after leaving Ireland, but he eventually lived in eastern Dorchester. Daniel Sulivane of Dorchester County, who lived there by 1708, seems to have been a native of Ireland. Although much of Ireland still practiced the Catholic faith, the Protestant Presbyterian faith became strong in the north, and most, although perhaps not all, of the early Irish settlers in Dorchester were Presbyterians (Mowbray 1984; Marshall 2025; Barnes et al. 1996–2025).

Several early Dorchester residents came from France. John and Margaret Gootee were French. Anthony LeCompte and wife Esther Dottando, natives of France who emigrated from London, settled first in Calvert County before traveling back to France. Upon their return to Maryland, they had settled in Dorchester by 1669. Milleson Marine, also a Frenchman, had settled initially in Virginia and then moved into Somerset County before settling in Dorchester County about 1670. Additionally, the Collier family of Nanticoke Hundred in Somerset and the Peter Dowdy family there were also Protestants of French origin (Mowbray 1984; Marshall 2025; Barnes et al. 1996–2025).

The French Huguenots and the Scottish and Irish Presbyterians, like the Puritans and Dutch already discussed, adhered to the teachings of the Swiss theologian John Calvin. Hence, an affinity sometimes existed between the two groups that may have influenced settlement patterns on the Eastern Shore. The Presbyterian faith in Dorchester seems to have been particularly strong in the later seventeenth and early eighteenth centuries, probably stemming from the late seventeenth and early eighteenth-century emigration from Scotland and northern Ireland of many Scottish and Ulster Scots Presbyterians. Historian Rankin Sherling has argued that the Presbyterian migration from Ulster to the Eastern Shore was a chain migration. Ulster congregants seem to have followed their ministers across the Atlantic with the result that entire congregations may have relocated over a period of years (Sherling 2015). This meant that earlier migrants were available to help later ones, a factor that promoted economic stability and social cohesion among the settlers. It also meant that, in contrast to the random nature of most recruited migrations through indentured servitude or forced migrations through enslavement, pre-existing family networks and kinship ties formed in Ireland and Scotland may have persisted on the Eastern Shore. In addition to a large number of Presbyterian settlers from Ulster, Charles Thompson of eastern Dorchester and several brothers emigrated from Scotland and settled in Dorchester County. One brother, Thomas, became a Presbyterian minister, and Dorchester County legal records show that he came from Tulliallan in Perth. These brothers also seem to have emigrated in a linked movement that spanned several years, and the will of Rev. Thomas Thompson indicates that kinship ties between Dorchester and Perth persisted into the eighteenth century (Jones 1925; Torrence 1935; Billings et al. 1986; Land 1981; Mowbray 1984; Barnes et al. 1996–2025).

A substantial number of early Dorchester settlers had Scottish or Irish connections. Many of them had probably been among the Ulster migrants who settled in Somerset County in the late seventeenth-century, and by the early eighteenth-century settlers often called Island Creek in southern Dorchester Ireland Creek (McAllister 2002), probably a byproduct of the heavy Irish influence in some parts of the county. More clearly than with the north to south migration, the westward migration into Dorchester demonstrates the possibility for large scale cultural persistence among migrants and the persistence of family and kinship networks spanning the Atlantic divide. While speculative, this may have been the case even among the indentured laborers who arrived in the area since men like Stevens and Browne seem to have recruited workers from northern Ireland and southwestern Scotland who were likely joining friends and relations that had already made the journey to Maryland. The presence of substantial, well-established family and religious networks among many of those who arrived in Dorchester County from the east attests to the role social networks played within this migration pattern. Although Ravenstein argued that migrations often occur in stages over prolonged periods of time, with other migrants later following similar routes, he did not emphasize the role of social networks in recruiting migrants or in facilitating migration and settlement themselves (Ravenstein 1876, 1885, 1889). As with the Loockermans, in later generations these families would mix with other population groups as continued transatlantic migration to the region declined. But the continued presence of Presbyterianism on the Eastern Shore demonstrates elements of cultural persistence among the Ulster Scots population in the region despite the overall tendency towards cultural fluidity and hybridization prevalent in many Atlantic societies (Greene 1988, 1993; Egerton et al. 2007).

6. Migration from the West

A substantial component of early Dorchester County migration proceeded along a trajectory from west to east that differed more significantly from the migration trajectories typical for much of American history. Maryland’s first settlements took place in St. Mary’s County, formed in 1637, three years after the group of settlers arrived in the colony. St. Mary’s City, formed in 1634, served as the colony’s capital until 1695. Settlers located the town on the St. Mary’s River, in the middle of the large peninsula between the Potomac and Patuxent Rivers. As settlement increased, colonists moved out from St. Mary’s City into the north, west, and also east (Land 1981; Mowbray 1984; Barnes et al. 1996–2025; Russo and Russo 2012).

To the east, across the Patuxent River and Chesapeake Bay, lay a large coastline punctuated with small islands and riverways that belonged to the Nanticoke people, one of the region’s early Native American groups. Settlers began to carve out land in this area by the early 1660s, and a 1 May 1668 treaty conveyed much of the Nanticoke land to the colony after two decades of intermittent conflict. While some colonists had already ventured into Nanticoke territory, the 1668 treaty officially opened a much larger area to settlement (Rountree and Davidson 1997; Mowbray and Mowbray 1992; Jones 1925).

A substantial number of settlers ventured eastward across the Patuxent River from the older, longer settled western counties of St. Mary’s, Charles, Calvert, Anne Arundel, and Baltimore. These settlers were mostly, but not entirely, of English origin. Most were Protestant, but the migrants from the west did include several early Catholic families who had settled originally closer to St. Mary’s on the west side of the Patuxent (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025).

Settlers from the western shore of the Patuxent River seem to have been the largest component of the initial settlement of Dorchester County. When lands first opened, a significant influx of settlers arrived from the west. Several reasons help explain this. Already established families would have been better acclimated to Maryland’s political, social, and economic systems. Some would have already prospered and thus would have had both the knowledge and the resources to seek land in areas first opening to new settlement. In addition, many of these migrants came to the colony in the middle 1630s. By the 1650s and 1660s, their offspring were coming of age at a time when lands in the longer settled region west of the Patuxent were becoming scarce. This no doubt prompted many more prosperous colonists to invest or speculate in lands that they could develop for a profit or that they could hold onto for their children and grandchildren to support future generations of their families (Russo and Russo 2012; Land 1981; Mowbray 1984; Mowbray and Mowbray 1992; Carr et al. 1991).

The west to east migration route thus demonstrates the push and pull factors associated with much scholarship on migration history (Catapano 2025). At the same time as population growth expanded and the supply of available lands dwindled on the western side of the Chesapeake Bay, new territories opened on the eastern side that promised to relieve these pressures. In contrast to Ravenstein’s focus on urban attraction, a combination of economic motivations to own and cultivate land and a desire for greater religious autonomy seems to have brought migrants eastward across the bay, including Catholics and Protestant dissenters who had already relocated to the western shore from elsewhere. As Calvin and Mary Mowbray demonstrated, within the first decade of Dorchester’s settlement, a substantial number of land grants distributed sizeable tracts along its Chesapeake shoreline as well as on many of its major rivers (Mowbray 1984).

St. Mary’s County, the first county created in colonial Maryland, originally extended north of its present boundary into the interior region. In 1650, parts of St. Mary’s became Charles County, later renamed Calvert in 1654, and Anne Arundel County, located to the north of Charles County. The settlers who arrived in Dorchester from across the bay in the 1650s and 1660s included many families that had settled along the Patuxent River in the 1630s. Through marriage, family networks formed there that migrants who settled in Dorchester then transplanted across the bay. The case of John Rawlins, who settled in Dorchester in 1668, provides an example. Rawlins seems to have been born in Maryland in the early 1640s following the arrival of his parents. Rawlins appeared in Dorchester by 1668 as part of a chain migration of relatives that would eventually include his mother, stepfather, siblings, wife, stepchildren, and their families. In the next generation, Rawlins’ children married into the Gray, Newton, and Fisher families that had also entered Dorchester from across the bay. By the end of the seventeenth century, an extensive kinship network had formed that included half a dozen second and third generation Maryland families with ties to the early Patuxent River settlements on the western side of the colony (Mowbray and Mowbray 1992; Mowbray 1984; Barnes et al. 1996–2025).

The names of many of the early settlers who arrived from the west side of the Patuxent River appear in

Table 3. This table shows the names of some of the early colonists who came to Dorchester from the western counties. Most early migrants in this group came from Calvert County, although a few came from Baltimore and St. Mary’s Counties. Dates reflect the occurrence of their name in deed, land grant, court, probate, or other documents and may have preceded their actual arrival in the colony. In some cases, dates have been estimated based on a subsequent appearance in such documents. (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025; Coldham 2002).

Name	County of Previous Residence	Date by Which They Appeared in Dorchester
Isaac Abraham	Calvert5	1663
George Anderson	Calvert	1665
Francis Armstrong	Calvert	1657
John Ashcom	Calvert	1669
John Atkins	Calvert	1668
Richard Blinkhorne	Calvert	1673
Michael Brooke	Calvert	1662
George Bussey	Calvert	1659
William Chapline	Calvert	1659
William Dorrington	Calvert	1663
John Edmondson	Calvert	1664
Sarah Preston Ford Pinder	Calvert	1670
Stephen Gary	Calvert	1662
Phillip Griffin	Anne Arundel	1700
Henry Hill	Anne Arundel	1699
Henry Hooper	Calvert	1668
Thomas Hooten	Calvert	1667
Hugh Hopewell	Calvert	1665
Keene Family	Calvert	1694
Anthony LeCompte	Calvert	1669
Edward Lloyd	Anne Arundel	1662
Thomas Manning	Calvert	1658
Timothy McNamara	Calvert	1677
Henry Mitchell	Calvert	1685
James Mullikan	Calvert	1666
Patrick Mullikan	Calvert	1662
Henry Osborne	Calvert	1667
John Pollard	Calvert	1669
John Rawlins	Calvert	1668
Peter Sharp	Calvert	1672
Raymond Staplefort	Calvert	1667
William Stevens	Calvert	1670
John Taylor	Calvert	1668
Thomas Taylor	Calvert	1665
Thomas Todd6	Baltimore	1690
William Travers	Calvert	1679

.

Most of those who acquired land in Dorchester either moved there or kept it for their children, who moved there. Some remained absentee owners and may never have lived in the county. An example of an absentee owner is Governor William Stone. Stone came first to Virginia, where he lived by 1633. He later settled in Accomack and Northampton Counties there before moving to Calvert County, Maryland. At the time of his death about 1676, he lived north of St. Mary’s in Charles County. Stone had begun acquiring land in Dorchester in the 1660s, however, and several family members settled and established trading connections in the area over time. Members of Edward Lloyd’s family followed a similar pattern. They did move to the Eastern Shore, but they settled on a plantation called Wye in Talbot County. The Lloyds owned land in Dorchester and appear in Dorchester records, but they seem to have primarily resided in Talbot County throughout the colonial period (Mowbray 1984; Barnes et al. 1996–2025; Yentsch 1994).

The Thomas Taylor family of Dorchester provides an example of what historians Darrett and Anita Rutman termed the “cosmopolitan few” (Rutman and Rutman 1984b, 1984a). The second generation of a family that had entered the colony much earlier, Taylor settled in Dorchester by about 1665. His uncle Cuthbert Fenwick had been an early Maryland settler, and Fenwick’s sister Jane—Thomas Taylor’s mother—had married Thomas Smith of St. Mary’s by 1635. When Smith died, she married William Eltonhead, a prominent early Maryland resident. Eltonhead had come from Preston in Lancashire, England, and several of his siblings settled in the colonial Chesapeake. Through the marriages of his sisters, Eltonhead was a brother-in-law of Ralph Wormeley, Henry Corbin, William Brocas, and John Carter, all members of the Virginia Governor’s Council. When Eltonhead died, Jane Fenwick then married Thomas Taylor’s father. Each marriage meant a consolidation of properties, which the new husband controlled. The family lived at Kent Island and in St. Mary’s and Calvert counties for two decades before Taylor and his descendants moved into Dorchester. They always retained a broad network of relations and business associates that included prominent residents of both Virginia and Maryland (Hayden 1891). This distinguished them from many other early colonists with smaller and less prominent social networks.

Edward Lloyd offers a similar example. Lloyd had moved to Providence, now Annapolis, Maryland, from Virginia with the Puritan settlers in 1649. Although he returned briefly to London in 1668, Lloyd began acquiring property in the frontier area near the present-day boundary between Talbot and Dorchester Counties in 1662. His descendants retained property in the area and lived primarily in Talbot County, but they mixed with some of Maryland’s leading families on both sides of the Patuxent River. In later generations, these descendants included three of Maryland’s governors and individuals prominent politically, socially, and economically throughout the colony’s early history (Mowbray 1984; Yentsch 1994).

The west to east migration route into Dorchester thus contributed to the region’s cultural complexity by transplanting well-established families from the western side of the Chesapeake Bay onto the Eastern Shore. These included second and third generation Maryland residents, many of whom were born in the colony. Most had English origins, and many moved into the county as part of an extensive migration of interrelated social networks. At the apex of this group were figures already prominent in the region like William Stone, Edward Lloyd, and members of the Fenwick-Eltonhead-Taylor kinship group. These individuals moved outside the narrower confines of individual locales and often held office at the colony level that positioned them within England’s transatlantic imperial framework. Others were the more modest children and grandchildren of small planters who sought to improve their circumstances across the bay in Dorchester. For those born in the colony, migration into Dorchester often became the first step in their personal journeys. Nevertheless, it represented an additional phase in a familial migration trajectory that in the previous half century had included transatlantic migration and one or more previous migrations within the colonial Chesapeake. In contrast to Ravenstein’s emphasis on rural to urban migration and the role of young, single men as migrants (Ravenstein 1876, 1885, 1889), family and religious networks seem to have played a critical role in this migration trajectory. Mature families and extended kinship networks relocated to Dorchester, where they acquired tracts to support their families through farming, planting tobacco for commercial purposes, trade, and maritime activities.

7. Migration from the South

The last major migration route into Dorchester County followed a south to north migration trajectory (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025). Such migration patterns are not unknown in American history. Large urban centers like New York, Philadelphia, or Chicago often drew settlers from the surrounding area and tended to attract migrants from significant distances in every direction. Outside these urban areas, however, the economic prospects offered by the availability of new lands during settlement periods also shaped migration routes that headed northward. Some early New England colonists moved west and northwest into French Canada. During the nineteenth century, the opening of the Northwest Territory and, later, the Pacific Northwest, also drew migrants from more southerly locations (Catapano 2025).

Availability of new lands on the Eastern Shore seems to have been a key factor in migration into Dorchester from the south. To a lesser degree, Maryland’s more tolerant religious views may also have played a role. The region attracted Quakers, Presbyterians, Puritans, and other Calvinist faiths in addition to members of the Church of England and persecuted Catholics. Founded initially as a haven for persecuted Catholics in England, Maryland in 1649 passed “An Act Concerning Religion.” Today called the “Toleration Act,” this piece of legislation “granted freedom of conscience to all Christians.” Along with Governor Stone’s open invitation to fellow Puritans, this act seems to have been the impetus for many dissenters to move into Maryland from other locations (Finkelman 2006; Land 1981; Maryland State Archives 2025).

The maritime culture of the Chesapeake Bay region facilitated northward migration from Virginia by sea as well as by land. In terms of migration by land, some settlers moved north out of Accomack and Northampton Counties on the lower eastern shore. Accomack County, one of Virginia’s original counties formed in 1634, included early English settlements that dated to the second decade of the seventeenth century. In some cases, families moved first into Somerset County before settling in Dorchester; in others, they seem to have moved directly from Accomack and Northampton into Dorchester without ever having lived in Somerset, possibly traveling part of the way by sea (Mowbray 1984; Thomas 2004; Curtin et al. 2001; Torrence 1935). This unusual migration pattern contrasts with Ravenstein’s migration laws in that there seems to have been no urban pull drawing settlers northwards (Ravenstein 1876, 1885, 1889). Instead, economic and religious motivations were paramount.

Outside migration from the lower Eastern Shore, other Virginians moved from the lower, middle, and upper peninsulas of Virginia or the south side of the James River into Dorchester. These settlers likely traveled by sea, some of them perhaps all the way to Dorchester. Others may have ferried to the lower peninsula and traveled north by land into Dorchester. The exact place of residence in Virginia of some early Dorchester residents is unknown. Importation records often note only that the colonist entered the colony “from Virginia.” But for some settlers, however, deeds or other legal records document their places of origin prior to entering Maryland. Several settlers came from the upper peninsula counties between the Potomac and Rappahannock Rivers. Daniel Holland and George Thompson had lived in Northumberland County, and the Dickenson family came from Lancaster. Like the Lloyds and Stones, the Lee family were absentee owners. John Lee of Westmoreland Co., VA, acquired the tract known as Rehoboth in Dorchester in 1673. It remained in the family’s possession after the colonial period had ended. When John Lee died, it passed to his brother Richard Lee of Stratford Hall, progenitor of the distinguished Lee family of Virginia. Over the next seventy years, the family subdivided the land into several smaller tracts, all also called Rehoboth. Richard Lee’s family, including Governor Thomas Sim Lee of Frederick Co., MD, still retained the land at the time of the American Revolution. In the 1780s, John Smoot, a wealthy merchant and planter, acquired much of the tract, which still continued to be associated with the Lee name (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025; Marshall 2025; Miles 2025; Maryland Historical Trust 2013.

Proximity to the upper peninsula may have facilitated emigration and absentee management from residents there into Dorchester, but some Virginians came from further south. Mary Hayward Ennalls and her family moved into Dorchester by about 1668 from York County, Virginia, on Virginia’s lower peninsula. Thomas Manning came from even further afield. Manning had originally lived in Nansemond County, south of the James River and bordering on the Carolina territory. Manning’s journey of more than one hundred and fifty miles, which included a period of residence in Calvert Co., MD, on the western side of the Chesapeake Bay, could only have occurred by boat (Mowbray 1984; Barnes et al. 1996–2025).

Families like the Lee, Hayward, and Ennalls families already possessed substantial resources when they acquired property in Dorchester. They became even more affluent over time. The primary seat of the Lee family continued to be Stratford Hall, overlooking the Potomac River in Westmoreland County, Virginia, but the Lees retained an interest in the land and the development of the 2350-acre tract in Dorchester. Impermanence characterized much Chesapeake architecture, but a house—still standing, and variously called Rehoboth, Liberty Hall, Turpin Place, and Lee Mansion—was built there between 1771 and 1790, possibly to replace an older structure that had been destroyed (Maryland Historical Trust 2013; Carson et al. 1991).

Mary Hawyard Ennalls was the widow of Francis Hayward of York County, Virginia, who wrote his will there in 1657. The family had less money than the Lee family, but Francis Hayward prospered in Virginia and left property to his wife and sons. His widow Mary married Bartholomew Ennalls in York shortly after her first husband died. Virginia records show that they had three children born there between 1665 and 1668. Following the birth of their third child, Mary Hayward Ennalls and her husband Bartholomew relocated their household northward. This included Mary’s two Hayward sons, Mary and Bartholomew’s four Ennalls children, and three servants—John Nicholls, William Snellock, and Susan Hide—who together entered Dorchester County “from Virginia” (Mowbray 1984).

Over time, the family continued to prosper. Thomas Ennalls, the first son of Bartholomew and Mary, became a planter and merchant with an extensive transatlantic trade. He represented Dorchester County in the Maryland Assembly in 1692 and served in the lower house from 1692 to 1702. At that time, he received an appointment to serve as a member of the Maryland Governor’s Council, one of the highest offices that colonials could attain. Ennalls held that position from 1703 to 1718. Ennalls also served as a justice of the Dorchester County court from 1690 until 1703 and as a militia officer from 1690 until 1718. This culminated in his role as colonel, a military position that paralleled his political one at the apex of local society. When he died in 1718, Thomas Ennalls owned about 5000 acres of land, thirty-eight slaves, and personal estate (including those slaves) inventoried at £4661.17.11. Several members of the family sat in Maryland’s colonial Assembly. Over time, the Ennalls family intermarried with other prominent Dorchester families like the Woolfords, Hollands, Loockermans, Brookes, and Goldsboroughs to form a powerful political and economic network in colonial Dorchester. These included other slaveowners like the Ennalls family. Many of them also owned land and plantations outside the county that supplemented their family’s wealth. By the end of the colonial period, at the apex of this group were members of the greater Chesapeake gentry. This included families like the Ennallses who often had social, economic, political, and family connections outside the county and sometimes outside the colony that linked them to other elite slave-owning families (Papenfuse et al. 1979; Mowbray 1984; Barnes et al. 1996–2025; Isaac 1982).

A representative sample of the names of early Dorchester settlers who came to Dorchester from Virginia appears in

Table 4. Virginia colonists who settled in Dorchester. The list is representative but not exhaustive. Dates reflect the occurrence of their name in deed, land grant, court, probate, or other documents and may have preceded their actual arrival in the colony. In some cases, dates have been estimated based on a subsequent appearance in such documents. (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025; Coldham 2002).

Name	Prior Residence	Date by Which in Dorchester
Daniel Clarke	Virginia7	1665
Nehemiah Covington	Virginia (Northampton)	1695
Mary Hooper Chapline	Virginia	1659
Walter Dickenson	Virginia (Lancaster)	1666
Mary Hayward Ennalls	Virginia (York)	1668
Thomas Fowkes, Chirurgeon	Virginia (Accomack)	1680
John and Francis Hayward	Virginia (York)	1668
Susan Hide	Virginia (York)	1668
Daniel Holland	Virginia (Northumberland)	1670
Henry Hooper	Virginia	1679
John Lee	Virginia (Westmoreland)	1673
Thomas Manning	Virginia (Nansemond)	1660
John Nicholls	Virginia (York)	1668
William Merchant	Virginia	1666
Richard Preston	Virginia (Norfolk)	1649
Dr. Peter Sharp	Virginia	1672
Thomas Skinner	Virginia	1666
William Snellock	Virginia (York)	1668
Anthony Tall	Virginia	1669
George Thompson	Virginia (Northumberland)	1664
William Willoughby	Virginia	1672
Thomas Wingate	Virginia	1683
Roger Woolford	Virginia	1704
Ishmael Wright	Virginia	1665

.

In contrast to Mary Hayward Ennalls and Thomas Manning, migrants like Dr. Peter Sharp are difficult to classify. Like John Lee, they did not establish permanent residence in Dorchester despite acquiring land in there and appearing in legal records. Sharp came from Virginia but first to Calvert County on the western side of the Patuxent River. He died there about 1672, but he acquired land in both Talbot and Dorchester Counties. He seems to have traveled between Dorchester and Calvert Counties but to have maintained his primary residence in Calvert. Instead, his children and grandchildren permanently relocated to Dorchester and left many descendants there. Sharp’s initial interest in Maryland may have been religiously motivated, and he may have viewed Dorchester and Talbot County as places of even greater religious freedom than the western settlements. When he first arrived in Maryland, Sharp practiced Puritanism, but over time he adopted the Quaker faith. This factor in particular may have attracted him to southern Talbot and northern Dorchester Counties, where the Third Haven Monthly meeting had a strong base (Third Haven Monthly Meeting 1940; Mowbray 1984). As with the Wheatley example, this sort of circular, back-and-forth migration offers a contrast with more direct migration routes that nuances Ravenstein’s emphasis on step migration proceeding towards the ultimate destination (Ravenstein 1876, 1885, 1889).

Migration from Virginia brought a mix of settlers into Dorchester. Most were of English background, and most tended to follow the Church of England’s teachings. They had primarily come north in search of land and enhanced opportunities. In some instances, like the Lee family, they were initially absentee owners who managed their properties from across the Chesapeake Bay, but, in most cases, they settled in Dorchester and became permanent residents. Some of the settlers were aspiring young planters on the make. Others, like the Ennalls brothers and the Lee family, belonged to the group that historian Bernard Bailyn described as that from which the colonial “gentry” formed, those close enough to the upper echelons of society to “feel the pangs of deprivation most acutely.” For individuals like Thomas Ennalls and his family, Dorchester became the path to immense success (Mowbray 1984; Smith 1959, reprint 2014).

As with the other regional migrations discussed, a substantial number of these migrants were religiously motivated, a factor that played little role in Ravenstein’s analysis (Ravenstein 1885, 1889). They may have had economic motivations as well, but the relative religious freedom offered in Maryland, particularly in this sparsely settled area of the Eastern Shore, seems to have been the driving factor that prompted them to relocate. Unlike the Lees, who already had substantial resources, such a move may have brought financial risks for many of these less prosperous individuals due to the costs of relocating across the bay with their families.

8. Culture and Migration

Migration into colonial Dorchester County, Maryland, played a critical role in the cultural development of Dorchester and surrounding areas of the Eastern Shore. Much of the remaining Chesapeake region tended to be culturally homogenous, and historian David Hackett Fischer has argued that early settlers transported the culture of southeastern England—the so-called “Home Counties”—to the seventeenth century Chesapeake while settlers from East Anglia transplanted a very different regional culture to the New England colonies. Although both regions were primarily settled by the English, Fischer argues that English regional cultures played a fundamental role in who went to each of these two new world regions and in terms of the cultures and societies that developed there (Fischer 1989).

Within Fischer’s paradigm, colonial Maryland, including the Eastern Shore, fell within the zone where the folkways of southeastern England predominated. Among the weaknesses in Fischer’s approach are that it fails to accommodate the non-British elements that contributed to the formation of culture in society in colonial British America and that it fails to explain how those cultures might evolve and mix over time into a new, blended culture. In colonial Maryland’s plantation-based economy, initially indentured laborers and later slaves worked these tobacco plantations. But significant differences existed that helped shape the culture of the Eastern Shore and that distinguished it from other regions of the Chesapeake, despite a shared political and economic system (Fischer 1989; Russo and Russo 2012). One of these was the presence of mixed agriculture, small farming, coastal trade, and shipbuilding that, because of the region’s geography, prospered in areas where a tobacco-based plantation economy did not dominate. Another was the migration routes that brought settlers into Dorchester in substantial numbers from the north, south, east, and west. This was unlike other parts of the Chesapeake and lower South, where the predominant routes migrants took led from the eastern Tidewater region west into the interior Piedmont and Backcountry regions and north to south, from New England and the Middle Colonies. This type of north to south migration, often characterized by a southwesterly route, also moved settlers from the Chesapeake into the Lower South and from one part of the region to another.

In terms of the distinctiveness of the Eastern Shore, this meant that, unlike other parts of the Chesapeake, particularly other parts of the eastern Tidewater region, a substantially mixed society developed. Religiously, colonial Dorchester included Quakers, Puritans, Presbyterians, French Protestants, Catholics, and adherents to the established Church of England. Culturally, settlers from the northern colonies—some with Dutch or Swedish heritage—mixed with settlers from Ireland, Scotland, France, and England. This did include many who hailed from Fischer’s southeastern counties, but it also included setters from other parts of England as well. Many of these families were the second or third generation in America by the time they reached Dorchester in the 1660s, 1670s, or 1680s, although some had come directly from Europe into the region (Mowbray 1984; Mowbray and Mowbray 1992; Barnes et al. 1996–2025). And, very significantly, descendants of these European-American cultures mixed with enslaved and free black families of African heritage. Many of them also interacted with Native Americans, who remained on the Eastern Shore in substantial numbers (Davidson 1991; Heinegg 2000; Rountree and Davidson 1997; McAllister 1962).

Well into the eighteenth-century, Dorchester records identified individuals of Native American origin. Many of these bore European names, like Thomas Corsey, Peter Monk, Thomas Bishop, William Corhunk, and John Puckham (McAllister 1962, 2002; Rountree and Davidson 1997). In some cases, these cultures mixed further, such as when John Puckham, a Nanticoke Indian man, married Joan Johnson, granddaughter of Anthony Johnson, a free black man who lived on the Eastern Shore (Rountree and Davidson 1997; Davidson 1991; Heinegg 2000; Breen and Innes [1980] 2005). Puckham—whose name may have been an Anglicization of the Nanticoke name Puckamee—and Johnson both bore surnames that reflected English cultural influence, but they were part of a large number of mixed-race families on the Eastern Shore. Some of these had surnames that evidence Spanish or Portuguese connections, including the Sisco, Driggers, Consellor, and Songo families that continued to intermarry and associate together for generations (Davidson 1991; Rountree and Davidson 1997; Heinegg 2000; Breen and Innes [1980] 2005; Russell 2001; Goetz 2016).

Further examples of this mixing of cultural influences are evident in the family histories of two of the most well-known Eastern Shore natives, Harriet Tubman and Frederick Douglass. Harriet Tubman, named Araminta Ross at birth, was born in Dorchester County in March 1822, a daughter of Benjamin Ross and Henrietta Green, called Rit. Harriet married John Tubman, a free black man born in Dorchester County in 1820. Harriet may have been of Ashanti heritage through her maternal grandmother, who reportedly came from Africa’s Gold Coast region (Clinton 2004; Larson 2003, 2004). But her father’s surname, Ross, Scottish in origin, suggests a link to John Ross, who had settled on the Little Choptank River in 1677. And the name of her husband John Tubman suggests a connection to the English Catholic Tubman family of Richard Tubman and Eleanor Staplefort, who entered Dorchester County about 1670 from Calvert County on the west side of the Patuxent River. African American naming customs during and immediately after slavery were complex. The use of surnames could reflect a family connection, either paternal or maternal, a connection to the family of an enslaver, or a self-chosen surname (Williamson 2020). The use of the names Ross and Tubman, then, could indicate any one of several possible relationships.

Frederick Douglass, born Frederick Augustus Washington Bailey in 1818, came from Talbot County, a few miles north of Dorchester. He grew up on Wye Plantation in the Tuckahoe Creek area of Talbot County, about thirty-five miles from where Tubman lived near the northern coast of Dorchester in the Madison area. As shown in the section on migration from the north, many settlers moved south from Talbot. As with neighboring Somerset to the east, this often involved a circular, back-and-forth migration that saw families move into and out of Dorchester over time. Although born on Col. Edward Lloyd’s plantation, Douglass legally belonged to Lloyd’s overseer, Aaron Anthony, who may have been his father. Douglass bore the surname of his mother, Harriet Bailey, daughter of Isaac Bailey, a free black man, and his wife Betsey, an enslaved woman. Douglass grew up in his grandparents’ cabin and lived there with them until about age eight, when he began to work on the Lloyd plantation himself. Like many families in southern Talbot County, the Lloyd and Anthony families both had ties to colonial Dorchester, and it is not improbable that Isaac and Betsey Bailey also did8 (Douglass 2020, 1892; Foner 1964; Mowbray 1984).

As the cases of Douglass and Tubman show, a mixing of cultures did not imply that an egalitarian society would develop as a result. Douglass and Tubman both endured harsh conditions, eloquently recorded by Douglass in his autobiographies. Both also found life as slaves on Eastern Shore plantations so cruel, exploitative, and oppressive that they risked their lives to escape and to lead others to freedom. Colonial Dorchester society, with families like the Ennallses and Brookes at its apex and a substantial enslaved population at its base, was far from equal, and the sorts of cultural mixing reflected in the names and backgrounds of Douglass and Tubman involved physical and emotional violence and exploitation of the harshest kind (Douglass 1892, 2020; Larson 2003, 2004; Clinton 2004).

Although this study has focused primarily on European-American migrations and the cultural connections among those migrants, it is important to acknowledge that a full account of cultural development in the region would also incorporate the mixing of African-American and European-American cultures and interactions with the Native American groups on the Eastern Shore. Scholars like Mechel Sobel, writing in the context of Chesapeake society, Anne Yentsch, writing about colonial Talbot County, Maryland, and Sidney Mintz, writing about African American culture more generally, have examined aspects of that process in terms of the formation of African American society and the mixing of “Black and White Values” in the colonial Chesapeake. Sobel argues for the formation of a regional culture that combined folkways and thought systems that originated in Africa with others coming from European society, and Anne Yentsch, examining the Wye House plantation in Talbot County, Maryland, found evidence of cultural syncretism that combined West African and English cultural practices such as in material culture, foodways, domestic space, and religion (Sobel 1988; Yentsch 1994; Mintz 1992). Ira Berlin has also examined figures like Anthony Johnson and Emmanuel Driggers, whose descendants came into Dorchester, as part of the group he terms “Atlantic Creoles”. Individuals like Driggers may have had a combination of African ancestry and European heritage, as the name Driggers, derived from the Spanish or Portuguese Rodriguez or Rodrigues, suggests. For them, residence on the Eastern Shore functioned as a further stage in an already complex migration journey that had begun elsewhere (Berlin 1998, 2003). A full study of the cultural complexity of Eastern Shore life would need to account for not only the blending of European-American cultures on the Eastern Shore but also for exchanges between those and peoples of non-European origins. This should include people of African heritage, free and enslaved, among them those Berlin terms “Atlantic Creoles” and the “Free African American” families Heinegg discussed. It should also consider the cultural influences of Native American figures like Puckham, Coursey, and others, who interacted, and sometimes intermarried, with these other groups. By the late colonial period, Eastern Shore families existed, free and enslaved, that combined ancestry from all three groups (Heinegg 2000).

The present study, more limited in scope, has examined European-American migration to draw attention to distinctive regional patterns and their consequences that might then serve as a foundation to further examine family development in the region as well as the intermixing of cultural folkways within Eastern Shore society. Among the European-American population, cultural mixture seems to have followed socio-economic lines but with some fluidity between ranks. The wealthy Loockermans from New Amsterdam, Dutch Protestants, intermarried with the Brooke and Ennalls families. The Scottish Thompson, Kirke, and MacKeele families intermarried with the English Phillips, Wright, and Wheatley families, all small to middling landowners who owned few, if any, slaves. Irishman William Geoghegan, said to have been a school teacher from Dublin, married Levina LeCompte, a descendant on her father’s side of Antoine LeCompte and Esther Dottando, French immigrants who had first settled in Calvert and St. Mary’s Counties and lived in Dorchester by 1673. On her mother’s and grandmother’s sides, Levina descended from Thomas Pattison and Thomas Skinner, settlers of British origin with ties to the North British borderlands region. Their later descendants had a mixture of Irish, French, English, and Scottish ancestry. Family members living in Dorchester during the late colonial period ranged from wealthy planters and politicians like Moses LeCompte (c. 1753–1801), a Dorchester justice and member of the Maryland legislature, to middling and small planters who exercised little political or social authority (Mowbray 1984; Papenfuse et al. 1979).

Although more research is needed on the social interactions among early Dorchester residents, evidence reviewed for this study suggests that despite the cultural variation among early Dorchester residents, the society that formed there solidified along socio-economic lines that tended to mirror the plantation-based, gentry-dominated culture of much of the other Tidewater region. But the resemblance was not absolute. Settled later than the western shore, Dorchester continued to receive an influx of migrants from elsewhere into the eighteenth century that included families of varied cultural backgrounds and socio-economic status. Early migrants from the western shore of the Patuxent River, many of them second or third generation Maryland residents by the time they reached Dorchester, carried cultural patterns with them to the Eastern Shore that had formed in the older, longer settled counties to the west, as did some of the early settlers who moved from Accomack and Northampton Counties in Virginia northward into Somerset and then westward into Dorchester. In this sense, as James Perry argued in The Formation of a Society on Virginia’s Eastern Shore, 1615–1655, and contrary to earlier interpretations of Chesapeake history that had stressed the fragility of a society plagued by political and social instability and early death, a politically and socially cohesive society took root early on that shaped the social and economic development of the region throughout the colonial and early national periods. But the examples provided by the Loockerman, LeCompte, and Ennalls families indicate that the relative cultural fluidity of early Dorchester allowed newcomers to prosper. Families like that of Jacob Loockerman retained elements of their distinctive past even as they negotiated a place for themselves among Dorchester’s local elite. And the presence of varied economic pursuits among a large number of families that did not own slaves limited the power and influence of “tobacco culture” (Breen 1985; Kulikoff 1986) throughout substantial parts of Dorchester.

Within this framework, for the European American colonists who settled there, colonial Dorchester offered a society where new elements could prosper socially and economically. Although families like the Ennallses and Brookes rose to become local gentry, the process took decades. Newcomers like Roger Woolford, who came into Dorchester from Somerset County to the east, Jacob Loockerman, who came into Dorchester from New Amsterdam to the north, Antoine LeCompte, a native of France who entered Dorchester from the western shore of the Patuxent River, and William Geoghagen, an arrival directly from Ireland, could become successful planters and political figures. They and their families shaped colonial Dorchester and the Eastern Shore across the seventeenth and eighteenth centuries (Mowbray 1984; Barnes et al. 1996–2025).

9. Beyond Dorchester: Conclusions

In discussing the laws of migration, Ravenstein noted the tendency of migrants to move incrementally, often today called step migration or stepwise migration, from one location to another rather than to initially undertake a vast move (Ravenstein 1876, 1885, 1889; Conway 1980; Catapano 2025). The examples in the previous paragraphs reflect that. Of the four cases mentioned, only Geoghagan, said to have sailed from Dublin, may have traveled from his point of origin into Dorchester directly, and thorough research into his background might reveal other stops along the way (Mowbray 1984). Thus, just as Dorchester was one of many stops for most of these early migrants, over time, their descendants began to leave the county. Influenced by Ravenstein, Waldo Tobler, in his “First Law of Geography,” articulated the idea that all things are connected but that near things are more connected than distant things, an idea also called distance decay (Miller 2004). In the tight-knit world of the Eastern Shore, a narrow peninsula surrounded by the Atlantic Ocean and the Chesapeake Bay with numerous interior riverways and creeks, connections between settlers, communities, and cultures were abundant and complex.

While some elements of Ravenstein’s theory apply to colonial Dorchester, significant differences exist. Early migration patterns suggest the continued importance of both step migration and chain migration. For most early Dorchester residents, settlement in Dorchester came as part of a process that had begun much earlier. Some migrants went to southern Virginia first. From there, they moved to the western side of the Chesapeake Bay. And from there they entered Dorchester when lands first opened for settlement. Many of them had been born in Europe, a journey that would have had multiple stops before embarking from a major port city. Social networks among migrants, a factor that received little emphasis from Ravenstein, played a key role in this migration, however. Extended kinship groups relocated from the western side of the bay, and religious networks such as those of Puritans from south of the James River and Quakers from the north seem to have shaped Dorchester settlement as part of an extended migration of related and associated families across a number of years (Mowbray 1984). This may also have been the case with migrants from northern Ireland. Although some arrived as indentured servants, recruiting networks on the Eastern Shore linked prominent merchant planters with trading networks in Glasgow and Dublin. Servants recruited from nearby villages may have influenced others to come later, especially since there is evidence that Irish Presbyterian congregations in many cases followed ministers like Francis Makemie and Thomas Wilson across the Atlantic onto the Eastern Shore. These individuals would have traveled with kinship networks that may have provided social, economic, and emotional support as they began their lives in Maryland (Sherling 2015).

Dorchester migration patterns also suggest other important deviations from Ravenstein’s model, however. Ravenstein ascribes primacy to the role of economic factors in shaping both the decision to migrate and the destination and route chosen. This was no doubt true for some early Dorchester settlers. But there were other motivating factors that existed outside Ravenstein’s paradigm (Ravenstein 1885, 1889). Among these were religious motivations, sometimes accompanied by social and political disenfranchisement as occurred in northern Ireland in the 1680s and 1690s. Maryland’s Toleration Act of 1648 extended welcome to dissenters. The act coincided with the opening of Dorchester lands for settlement in the early 1650s, even before the county’s legal formation. Social networks among fellow believers facilitated the migration, but the greater motivation seems to have been a desire to practice their faiths without persecution or prejudice. Quakers and Puritans came to the Eastern Shore in significant numbers, and the relative religious toleration likely influenced Dutch Calvinists like the Loockermans and French Protestants like the LeComptes to settle there as well. Religious motivations, and religious networks, do not figure prominently in Ravenstein’s analysis (Ravenstein 1885, 1889). Additionally, Ravenstein’s model stresses the importance of rural to urban migration. This factor is linked with a central thrust of Ravenstein’s overall argument about economic motivations, for in Ravenstein’s view cities offered greater prospects for economic security than elsewhere. The Chesapeake contained few cities and none that came close to rivaling the five major cosmopolitan centers of colonial British North America in size or influence. Instead, migration into early Dorchester suggested the opposite. Settlers like the LeComptes left the Huguenot settlements of London for uncertain prospects along the Maryland frontier, and the Loockermans traveled from New Amsterdam beyond Philadelphia to reach Dorchester. A desire for better economic prospects no doubt influenced their decisions, but this seems to have been only one of many overlapping factors that brought them into early Dorchester (Ravenstein 1876, 1885, 1889; Culver 1917).

Additionally, the case of colonial Dorchester also shows the importance of circular, back-and-forth migration routes. Early migrants from Somerset like the Wheatleys, Wrights, and Phillipses moved into and out of Dorchester multiple times across the decades. The same pattern appears among the residents near the Talbot County border of northern Dorchester. Some owned land in both counties, and others had friends and relations on both sides of the county line. For non-landowning renters, this sort of back-and-forth migration may have been more common, but even families with acreage in Dorchester seem to have traveled into and out of the county for substantial periods of time. This phenomenon may partially have been a function of Dorchester’s landscape. Some communities formed around bridges and ferries. Although rivers functioned as county boundaries, they did not always serve as physical barriers. Larger communities of trade, kinship, and religious association often spanned county boundaries. Settler movements across county lines thus seem to have been within the same local community, perhaps linked to the availability of suitable property for tenancy (Barnes et al. 1996–2025; McAllister 2002).

Early migration into Dorchester thus supports the idea of chain migration as a critical factor influencing regional settlement patterns. But Ravenstein (Ravenstein 1876, 1885, 1889) tended to underestimate the role of social networks, including religious, kinship, and commercial networks, in shaping migration. Additionally, his emphasis on rural to urban migration and step migration directed towards large urban centers fails to fit the pattern of Dorchester settlement, which included circular, back-and-forth migration along the county lines between Dorchester and Somerset and Dorchester and Talbot and rural to rural migration associated with mixed farming, trade, and plantation agriculture.

Most of the families who settled in seventeenth century Dorchester seem to have remained in the area for multiple generations. By the middle of the eighteenth-century, however, Dorchester residents had begun to leave the area in significant numbers. As had occurred with earlier Chesapeake migrations, by the middle eighteenth and early nineteenth centuries new lands opened in other regions just as the interior lands of the Eastern Shore filled to capacity. Additionally, population growth and family size increased competition for those lands. As had been the case with many of the first Dorchester Counties, limited economic prospects pushed third and fourth generation Dorchester families to consider options outside the region, and newly opened, more fertile lands to the south and west pulled them in those directions (Catapano 2025). The relative ease with which settlers could obtain frontier land offered economic prospects for younger sons and less well-off families, and the promise of bounty lands for soldiers after the Revolution provided an additional stimulus. These migrants tended to travel together in groups of related families, often followed by neighbors and close relatives as part of a chain migration that unfolded across decades.

One early migration route led southwest into Orange and Guilford Counties, North Carolina. Families like the Sullivans, Kirkhams, and Hacketts began to appear there in the 1760s and 1770s. A generation later, another route led further southwest, to Washington and Hancock Counties, Georgia. Families like the Walls, Bassetts, and Lords, most of whom appeared as renters in late colonial tax lists (Maryland State Archives 1999), began appearing on the Georgia frontier in the 1780s and 1790s (Ancestry.com 2010a, 2010b, 2011).

Following the American Revolution, the settlement of the Northwest Territory brought migrants west out of Dorchester into Kentucky and then into such places as Hamilton County, Ohio, Union County, Indiana, and Johnson County, Indiana. Describing the migration of the Wheatley family, Indiana historian D. D. Banta (Banta 1888) wrote:

Ezekiel Wheatley, farmer and stock-raiser, of Blue River Township, was born in the eastern part of Maryland [in]… 1817… [His father] William Wheatley… a soldier in the War of 1812… left Maryland in 1823, emigrating to Ohio and renting on the Big Miami fourteen miles north of Cincinnati, where his death occurred the year following. He was a farmer by occupation, and the father of six children… By the death of his father, Ezekiel Wheatley early in life was thrown upon his own resources, and for some years worked as a common laborer, contributing his earning to the support of his widowed mother and six orphan children. At the age of twenty-three, he married… [in] Franklin County, Ind., and for one year thereafter farmed in that county, and then moved to Hamilton County, Ohio…his home for four years.

Ezekiel eventually moved on to Johnson County, Indiana, south of Indianapolis, where he died. By the early twentieth century, his descendants lived in Indiana, Kansas, Oklahoma, and other western states (Banta 1888). By that time, descendants of Edward Wheatley who had followed other routes out of Dorchester lived in southwestern Virginia, Tennessee, Kentucky, the Carolina Piedmont, and states throughout the Lower South. In these new locations, they encountered cultural influences and regional traditions different from those they had known on the Eastern Shore. Through marriage and subsequent migration, they interacted with those new groups as their ancestors had done in Dorchester County, probably incorporating some aspects and influences while rejecting others.

While migration drew families like the Sullivans, Hacketts, Lords, and Wheatleys away from Dorchester, some family members remained there. Even today, these and other names tracing to the seventeenth century appear throughout Dorchester, Talbot, and Somerset Counties of Maryland and southern Delaware. A modern visitor strolling through the churchyard of Eldorado Methodist Church, nestled along the Nanticoke River in northeastern Dorchester near the Delaware line (an area once a part of Somerset County) will see gravestones, many of them recent, for families named Bassett, Wheatley, Lord, Hackett, and Marine, all families tracing to the settlement period that evidence the migration patterns discussed here. But despite the preference of many settlers for a system of partible inheritance that divided property and possessions among all heirs, older children often married, acquired land, and established themselves before their younger siblings came of age. This meant that younger siblings frequently migrated away to seek their fortunes elsewhere. And in some cases, setbacks—panics, economic depressions, bankruptcy, or other problems—could reverse a family’s fortunes and push even a successful and well-established family away. But, in most cases, early Dorchester families did not vanish entirely. They continued to be represented on the Eastern Shore, many even to the present day, while their cousins lived in places like North Carolina, Georgia, Kentucky, Ohio, Indiana, and Kansas, and eventually California, Oregon, and Washington.

Families of African-American and Native-American origin also left Dorchester and the Eastern Shore. Heinegg documents the presence of some mixed-race Eastern Shore families, including descendants of Emanuel Driggers, in North Carolina, South Carolina, and Virginia during the middle and late eighteenth-century. Members of many free black and Native American families simultaneously appeared in Dorchester Co., MD, Somerset Co., MD, Kent Co., DE, and Sussex Co., DE in the later eighteenth and early nineteenth centuries. This was true for the mixed-race descendants of Thomas Bishop, many of whom shared both Choptank Native-American and African-American heritage, as well as for descendants of John Puckham and Joan Johnson. The Consellar-Gonselea-Comsloe family, probably descendants of John and Grace Gonsolves who lived on the Eastern Shore by the 1670s, were especially numerous in Delaware, although some family members remained in Dorchester and Somerset. Families like the Driggers and Siscos, descendants of John Francisco, a Northampton Co., VA, slave in 1647 who later became free, began appearing by the early nineteenth-century in Georgia and Alabama, where census enumerations often recorded them as white (Heinegg 2000).

Heinegg also documents the presence of many mixed-race families from Dorchester and Somerset Counties in Ohio and southern Pennsylvania by the late eighteenth and early nineteenth centuries. This not only included the urban Philadelphia area but also rural farming counties (Heinegg 2000). These families had historically been free people of color. Escaped slaves also headed north for freedom in nearby areas. After leaving the Eastern Shore, Harriet Tubman and Frederick Douglass lived in Pennsylvania, New York, and Massachusetts for much or their adult lives. Other families of African-American heritage moved into Pennsylvania and New York from the Eastern Shore after emancipation (Clinton 2004; Larson 2003, 2004; Douglass 1892, 2020; Ancestry.com and The Church of Jesus Christ of Latter-Day Saints 2009, 2010).

The four migration routes that brought diverse groups of early settlers into colonial Dorchester blended settler cultures from the northern colonies with those of second and third generation migrants from southern Virginia, the western shore of the Chesapeake Bay, and the lower Eastern Shore. More recent arrivals in the Chesapeake who traveled directly from Europe added to this mix. This included not only migrants of English origin but families of Dutch, French, Irish, Scottish, and Welsh backgrounds. Even among those of English heritage, a large presence of religious dissenters existed that meant that settlers of Quaker heritage mixed with English Puritans, Dutch and French Calvinists, English and Irish Catholics, and members of the established Anglican church. In some cases, family identities shifted from one faith to another, as the example of the conversion of the Preston family from Puritanism to Quakerism shows. Over time, many of these individuals intermingled with the Native American and free African American communities, including Atlantic Creoles bearing surnames that evinced connections with Spain and Portugal, to create a notable mixed-race population on the Eastern Shore. This unique cultural configuration shaped the close-knit local communities of the Eastern Shore. But it also influenced other, very different regions of the country where migrants from Dorchester and their families settled in later generations. These included the former slaveholding states of the Lower South, the free states carved from the Northwest Territory, the midwestern states, whose settlers migrated from both regions, and the urban northeast. Historian Bernard Bailyn described the peopling of colonial British North America as one of the greatest population movements in human history (Bailyn 1988. It was, as Bailyn argued, a continuation of a process that had begun in the middle ages with the end of feudalism. Through four different regional migration routes, Atlantic World settlers of varied origins traveled into colonial Dorchester and contributed to its social, cultural, political, and economic development. Despite long residence on the Eastern Shore, for most of these families Dorchester County represented one phase in an ongoing cycle that would eventually move their descendants across the country. In contrast to the static model employed by David Hackett Fischer (Fischer 1989), this process of ongoing migration and cultural blending brought Dorchester folkways to other regions where they mixed with different populations in an ongoing process of cultural formation.