Introduction
The Choptank's waters, once pathways for the arrival and auction of enslaved African people, later became lifelines guiding daring escapes to freedom. Throughout America’s earliest years, Caroline County and the Choptank River bore witness to both the darkest chapters and the brightest hopes of Maryland's past. Locals like to boast that their lands are tied to some of history’s biggest heroes: Harriet Tubman, Frederick Douglas, and William Still. But why did settlers on the Eastern Shore seek out slave labor, what did the lives of the enslaved look like, and how did Maryland become the state with the most documented freedom-seekers? The answer lies in the existence of the “Great Choptank River”. This blog post delves into the Choptank River's role in the history of enslavement, emancipation, and the pursuit of freedom.
Historical Context
From the earliest days of European colonization, the Choptank River was crucial for transportation, trade, and sustenance, making it an indispensable resource for the burgeoning agricultural economy. It also proved extremely useful during the Revolutionary War, which you can read more about here. Both of these circumstances are factors in the story of enslavement and emancipation on the Shore, so let’s unpack that context first.
As Caroline County was forming in 1774, the American Colonies were spiraling out of control and becoming increasingly divided over the issue of British governance. Long story short, Caroline County quickly became one of the most Patriotic counties on the Shore. Because those affiliated with the Church of England were seen as British loyalists, and because the colonists had developed a dramatic distaste for anything tax-related, Anglicans in the area moved quickly to avoid being guilty by association. For the most part, Patriots tended to convert to Methodists, as its financial demands were much lower and it fit within the context of the new American identity. However, the Society of Friends, or Quakers, experienced a boom in membership as well. As much as your high school history teacher doesn’t want to admit it, a hefty percentage of colonists were against the Revolution for a multitude of individual reasons. Those who opposed the conflict for moral reasons, or just didn’t care to join in the Methodist migration, ended up Quaker. This religion was not new to the region- Easton had its first formal Quaker meet-up as early as 1676. As pacifists, Quakers were by definition abolitionists. This considerable population of Quakers in Caroline County would become entrenched in the fight against slavery, often directly aiding escaping slaves.
But why were enslaved people here in the first place? In the 17th and 18th centuries, the economy of the Mid-Atlantic region was heavily influenced by tobacco cultivation. This cash crop quickly became the cornerstone of Maryland's economy, driving settlers inland and up the Choptank River in search of fertile land. The river's rich floodplains and the Chesapeake Bay's temperate climate created ideal conditions for tobacco farming. The fertile soil, abundant water supply, and ease of transporting goods by water made the land along the Choptank highly desirable for planters looking to establish profitable plantations. However, the labor-intensive nature of tobacco farming necessitated a substantial workforce, leading to a growing reliance on enslaved labor. As the demand for tobacco soared, so did the need for enslaved Africans, who were forcibly brought to the Eastern Shore to meet the labor demands of plantation owners. Thus, Caroline County, with its prime agricultural land along the Choptank River, became a significant area for the expansion of slavery.
The script flipped when many of the Eastern Shore’s landowners realized that tobacco farming was not sustainable long-term. The plant was depleting the soil at much faster rates than other crops, and the land was becoming less and less plentiful as more planters moved in. Unlike the large, open areas of other colonies like the Carolinas, the Eastern Shore was surrounded by water. Therefore, these planters decided to phase out tobacco in favor of more forgiving crops such as wheat and corn. Many landowners no longer needed the large population of slaves they had required for the more difficult tobacco farming tasks, so they manumitted their slaves. This usually occurred upon the death of the landowner. Financial hardship caused by the Revolutionary War also meant that some white landowners freed their slaves as a means of reducing their overhead costs (feeding, housing, and clothing another person during one of the most economically devastating times in American history was almost impossible, let alone affordable). As a result, Caroline County became a rarity for its large numbers of free African American people.
The Role of the Choptank River in Enslavement and the Slave Trade in Caroline County
One of the greatest conveniences that the Choptank River offered during the pre-industrial era was the ease of transportation. People, animals, and goods flowed in easily from the Bay and into the Mid-Shore via the Choptank. This unfortunately meant that these waters carried many African people to their bondage during the Trans-Atlantic slave trade, stopping at least as far as the Choptank Lighthouse in Dorchester County.
Those who were sold at these stopping points would most likely board a second boat with their new enslaver, or with a career slave-trader who purchased in bulk to then hold their own localized auctions, and continue up the river to Caroline County. We know that the Caroline County courthouse was located in its present-day location when slave auctions occurred on its grounds. Men, women, and children were forced from their homes, carted across the sea in dangerously overpacked ships, and stood up in front of strangers who would calculate the worth of their lifetime in terms of profit margins. Loved ones were ripped apart, sometimes never to be seen again. Many African people who boarded the ships bound for the Chesapeake took their own lives- or tried to, or wished they had- before they could reach shore. What awaited these people was a life of abuse, dehumanization, and exploitation. The Caroline County courthouse grounds also hosted the jail where Underground Railroad agents and re-captured freedom seekers were held for their rebellion against the institution of slavery. Hugh Hazlett, an Irish fellow from Greensboro, was sentenced to 44 years in prison for helping a handful of slaves in Caroline County to escape in 1858- an example of the local justice system’s determination to uphold slavery even just a few years before the Civil War. Despite what you’ll read later about abolitionists in Caroline County, these lands and its people perpetuated the slave system, and for that reason we must hold ourselves accountable to tell the whole truth about our history; we must consider the true extent of our forefathers’ involvement and complicity in the institution of slavery, regardless of how many anti-slavery heroes Caroline County claims today.
At some point in the American psyche, this importation of African people became taboo. A majority of federal lawmakers agreed the trans-Atlantic slave trade should end- some for moral reasons, others for logistic ones. Hundreds of thousands of slaves already lived in the U.S. and the law declared that any children born to an enslaved mother would themselves be enslaved, therefore creating a constant supply. So, in a show of false moral superiority, congress decided to ban the importation of slaves in 1808 with the Act Prohibiting the Importation of Slaves. Localized slave trade, however, flourished.
A common phrase that sparked fear in the hearts of slaves in the area was the threat of being “sold down the river.” While the lives of slaves on the Eastern Shore were not sunshine and rainbows, they paled in comparison to those on sugar or rice plantations in the Carolinas or Louisiana. Many freedom seekers were motivated by catching wind of their enslaver’s plan to sell them “down the river.”
Enslaved people on the shore were both metaphorically and physically seen as chattel. In a 1781 tax assessment, each resident in “Choptank Hundred” (a district in Caroline County) listed their assets, including slaves. The eye-opening part of this document is where and how the slaves were documented: on the same chart as a landowner’s farm animals, without names (only sex and age), and with approximate values listed, as if nothing more than a piece of farm equipment or livestock. Similar dehumanizing language was used in the Last Will of slaveholders in the area. Peter Doutey, who died in 1710 in Dorchester (although it could have been present-day Caroline), gave specific instructions in his will as to his wishes for his slaves. Most had to work for a number of years before they would be granted freedom, others could be free but their children were to remain enslaved, etc. One might think that he was at least kind enough to provide eventual or partial freedom- but these sorts of requests were seldom ever honored. Harriet Tubman’s own parents had been promised freedom through a will, yet the family refused to abide by the dead master’s wishes. Anderson Eaton of Caroline County also included specific instructions for the sale or distribution of his slaves to his family members upon his death in March 1792.
A series of transcribed journals from the Willis family, who owned a large farm in Talbot County, gives glimpses into the lives of enslaved African Americans on the Eastern Shore. An entry from Feb. 9th 1850 reads “Nathan (a slave on the Willis’ farm) had become unruly and disobedient…tied Nathan and gave him 26 lashes with a black gum switch, which humbled him, and he promised to do better.” On this particular farm, enslaved people worked alongside hired help- usually free Black community members- which was common in the area and contributed greatly to the Underground Railroad’s success. Nathan was quite adamant about escaping slavery and aiding others to do so as well; he was found out to be planning to run away alongside slaves from surrounding plantations and was arrested for forging papers for freedom seekers in August of 1850. It was extremely unheard of for enslaved people to read and write (it was actually illegal to teach them in most states) because of this reason. Nathan was most likely writing “passes” for those attempting to escape which claimed the individual has permission to be traveling from their enslaver. Willis “brought Nathan home” and he continued to hold him in bondage until after the Civil War.
Unlike the Deep South, Maryland’s seasonal climate prevented year-round farming. White slaveholders on the Eastern Shore were constantly “hiring out” their slaves when they did not need them. Typical jobs for enslaved men on the shore included farming duties, spreading fertilizer (manure) by hand, building ships or docks, cutting timber, constructing buildings or roads, or working as temporary help to other whites. It was common to see a mill operator, for example, “hire out” an enslaved person during a particularly busy season or to help with a short-term project such as repairing a piece of equipment. Women were more prone to be hired out as they were usually assigned to more domestic roles such as house servants, cooks, or wet nurses. Whenever Susan Willis, the wife of the journal author I referenced in the above paragraph, had a baby, her husband hired out lactating enslaved women from his neighbors to feed and raise the said newborn. This sort of arrangement usually looked like this: a white woman gives birth, her husband pays a neighboring farmer $25 (plus the promise of clothing) to borrow his enslaved wet nurse for a year, after the year is up the wet nurse returns to her original enslaver or would be hired out by another postpartum white family, and so on. All the while these “hired out” individuals have no say in where they go, what they do, and who they work for. While this practice was uniquely cruel, it had unintended consequences for slaveholders. This shuffling of slaves gave them the gift of exposure, networking, ease of communication, and a broader sense of community- making their chances to pull off an escape much higher.
Free Black Americans, The Choptank River, The Underground Railroad, and the Pursuit of Freedom
There are plenty of reasons that Maryland holds the record for the state with the most escaped enslaved people- and almost all of them have to do with our plethora of waterways.
As I mentioned earlier, the Eastern Shore of Maryland had one of the largest free Black communities in any slave-holding territory. This population set up their own neighborhoods that endured for generations, such as the Hill Community in Talbot County, which formed in 1788. Like African Americans in the North, this free Black community found its niche in the maritime industry. If you were to look at the crew of a trade ship from Maryland to Maine pre-Civil War, you’d find a mixture of free African American sailors, slaves who were perhaps hired out by ship captains from their masters, and white laborers. The Chesapeake Bay was a major player in trade, both nationally and internationally, making the Bay and its rivers hotbeds for communication between free and enslaved African Americans. Smuggling of enslaved African Americans from the shore on these Northbound boats was rampant. If freedom-seekers couldn’t find a sympathetic boat captain or crew member, sneaking aboard was an enticing second option. Gilpin Point was a huge trade center in Caroline and became known throughout both pro and anti-slavery circles as a place where runaways could stow away on trade ships. This is just one of the ways that the Choptank became a tool for escape to the North.
One of the many free Black people living in Caroline County in the pre-Civil War era was James H. Webb. His log cabin, which he built in 1852, still stands outside of Preston. Webb’s home and persona are used today as educational tools to represent the lives of free Black Eastern Shore dwellers. The cabin itself is the size of a small studio apartment and it was handmade out of (probably leftover or scrap) ship-building materials. Despite its tininess, Webb lived there with his elderly father, his wife, and their four children. Something that one must keep in mind is that “free” does not mean “equal”, especially not in a border state. Despite there being many free African American residents, almost all of them would have lived this way, unable to climb the social and financial ladder due to discriminatory laws, unfair hiring and payment practices, disenfranchisement, and other hurdles caused by government-sanctioned racism and the unfortunate status quo. A surprising but not uncommon fact: Webb’s wife, Mary Ann, was a slave. And because the law required Black children to inherit the status of their mother, the Webb children were enslaved as well.
Marriage between free and enslaved Black people wasn’t unfamiliar. Whites all over the country encouraged their slaves to marry, as marriage meant procreation, and procreation meant more people to treat as property. This “allowance” of a basic human activity was used as an argument by slaveholders that they were kind to their slaves- a disgustingly contradictory statement. Over time, this system would backfire on pro-slavery whites in the Eastern Shore region. There is an interesting theory floating around that the reason that two of American history’s most celebrated freedom-seekers, Harriet Tubman and Frederick Douglas, were from the Eastern Shore was actually due to this prolonged exposure to free African Americans. In places like South Carolina and Georgia, there were almost no free African Americans. This is where a little bit of psychology and slaveholding strategy comes in. The enslaved people in these regions had no one to compare their livelihoods to, they were told that their place was slavery, and they didn’t see any evidence that there was another life possible for them because on much larger plantations in the Deep South, enslaved people rarely (if ever) left their holder’s property. This was in response to various uprisings by communities of enslaved peoples against their enslavers that were made possible because of intermingling between enslaved people with free sympathizers or with other enslaved people on different plantations. By isolating their human property as much as possible, white slaveholders were able to avoid the spread of information about escape. Communities were also much more unified in their support of the slave system, leaving freedom seekers with little assistance. Escape from the Deep South seemed futile and inaccessible, and quite obviously, the North was much farther away in comparison to Maryland. Of course, many did successfully flee these more Southern states, but those who did so had to navigate much trickier and more dangerous circumstances. These unique differences between the Eastern Shore and the Deep South are why historians, myself included, believe that the Eastern Shore became a place of mass escapism.
Back on the topic of enslaved / free marriage, did you know that Frederick Douglass' wife, Anna Murray, was from Denton?
She was the first child in her family born into freedom, as her parents, Bambarra and Mary Murray, were emancipated shortly before her birth. Anna Murray was born around 1813 and grew up in a free Black community in Denton. According to Anna and Frederick’s daughter, Anna’s parents had been enslaved by Maryland Governor Samuel Sprigg before gaining her freedom. Her status as a free woman allowed her to move to Baltimore and work for herself as a laundress, which led her to the shipyards where she met Frederick Douglass. This business is how she was able to gather the resources necessary for Douglass' successful flight to freedom, including money and a sailor's uniform to disguise him. After Douglass' successful escape, Anna joined him in New York, and they were married shortly after. Her courage and resourcefulness were instrumental in shaping Douglass' future as a leading abolitionist and orator- but it isn’t just her husband that makes her notable or admirable. Anna Murray-Douglass made significant contributions to the abolitionist cause. Anna worked as a laundress and learned shoemaking to support the family financially while Frederick traveled for his abolitionist speeches. She played a prominent role in the Boston Female Anti-Slavery Society. Later, in Rochester, New York, she transformed their home into an Underground Railroad station, offering shelter, food, and clean clothes to countless freedom seekers bound for Canada. While her husband refused to publicly acknowledge her significant impact on his life, her daughter Rosetta reminded those who admired her father that his story was made possible by the "unswerving loyalty of Anna Murray."
Unfortunately, white supremacist rhetoric was a powerful tool at the time, so powerful it penetrated even the minds of free African Americans on the Eastern Shore. Harriet Tubman’s first husband, John Tubman, was a free man from Poplar Neck who detested her escape and her aid of other freedom seekers. To him, a slave was property, unless they managed to free themselves the “right” way (by working side jobs to purchase their own freedom from their master or by waiting until their master freed them willingly). He hated his wife’s activities so much that he refused to go North with her in 1849, and by the time she came back, he had found another woman.
John Tubman serves as a reminder that just because the majority of Black people empathized with the enslaved, not all were exempt from participating. The very first free Black people to move to the Eastern Shore did so in 1661 or 1662. Their names were Anthony and Mary Johnson and they were slaveholders. Rixom Webb, most likely the father of the James Webb discussed earlier, owned a large property in Caroline County which he used slave labor to maintain. Rixom held at least six slaves, three on his property in Dorchester and three in Caroline. One of his Caroline estate’s slaves, Alfred, ran away in April of 1844, prompting him to publish a runaway ad in the newspaper offering a reward of $5 for his capture and return.
Rixom had purchased Alfred from Caroline County’s own Dr. Absalom Thompson, who happened to be the stepbrother of Harriet Tubman’s enslaver, Edward Brodess. Even though Rixom Webb played the role of a white landowner, his estate faced the reality of the racial hierarchy when his land was taxed after his death for the support of building Caroline County’s academy- a school his children would have been barred from entering. Even decades later, it would be a free Black man who turned in the Dover Eight, a group of eight escaped slaves who had been hidden by Harriet Tubman’s father Ben Ross at his home in Caroline County, to collect the bounty on their heads.
But for every unsupportive free Black person in Caroline County, there was a white abolitionist willing to put their life on the line to bring an end to slavery. A band of the most well-known Underground Railroad agents on the Shore was the Leverton family (Jacob and Hannah along with their son Arthur), who were Quakers. They oftentimes worked alongside a free Black man named Daniel Hubbard. Together, they operated in Caroline County, guiding freedom seekers through the area to safety. The Levertons, along with Hubbard, facilitated the escape of many enslaved people from Caroline County by using their home in Preston, MD as an Underground Railroad “station”. A misconception about the Underground Railroad system is that it was a tactile, real-life railroad. In reality, the Underground Railroad refers to a secret network of routes and safe houses used by enslaved African Americans to escape to free Northern states, Canada, or even Mexico. This network used railway terminology: "conductors" guided the escapees, "stations" or "depots" were safe houses, and "stationmasters" were those who managed these safe houses. The metaphorical language helped to disguise the topic of conversation among enslaved people and those involved with the Underground Railroad. Also, though she gets a deserved amount of fame for her bravery, Harriet Tubman was far from being the first or only UGRR “conductor”.
The Leverton house served as a beacon for Caroline County’s enslaved population. Its proximity to Lincester Mill, which still stands in Preston, is a considerable part of the reason why. The Choptank River and its tributaries made Caroline prime real estate for grist and sawmills- an industry that expectedly flourished in the area. Around 1840 a large water-powered mill, Linchester Mill, was built along Hunting Creek. The site, developed for its position on the creek, was the spot for many of Southern Caroline County’s daily operations. It was a place where free and enslaved people would have worked or ran errands side by side; a place where information flowed almost freely. If someone wanted to escape, they could find the right connections at the mill, and soon they’d find their way to the nearby Levertons, Hubbard, the Ross’ (Harriet Tubman’s parents in Poplar Neck), or the Kellys (another white Quaker family). For many freedom-seekers from below Preston, this was one of the last stops before reaching freedom. Self-liberating slaves, including those traveling with Harriet Tubman, followed the Choptank River up to Hunting Creek, using the local network of UGRR agents to provide a meal and a roof over their heads during the daylight hours. Once nightfall came again, they could easily cross Hunting Creek and make their way to Delaware and on up to Pennsylvania.
If you’ve spent this whole time wondering when I was going to talk about the three names in the introductory paragraph (Harriet Tubman, Frederick Douglass, and William Still), you’ve finally made it. Bear in mind these biographies are short and sweet- each of these people were more complex and influential than I have time to denote here.
Harriet Tubman was born Araminta Ross around 1822 in Dorchester County, Maryland to parents Harriet “Rit” and Ben Ross. She eventually took her mother’s name and married John Tubman, hence becoming Harriet Tubman. She was born into slavery and was enslaved by Edward Brodess. When Harriet was a teenager, she suffered a severe head injury that would affect her for the rest of her life. While trying to protect another enslaved person, she was hit in the head with a two-pound weight thrown by an overseer. This injury caused her to experience severe headaches, narcoleptic episodes, and vivid visions and dreams, which she interpreted as religious experiences. As a young girl she was frequently “hired out” to other slaveholders and, as a result, learned how to do almost anything. When she got word that she would likely be sold South after Brodess’ death, she devised a plan to run away. After escaping in 1849 she returned to the Eastern Shore numerous times (experts have pretty much decided on 13 times, but others claim it could be up to 19 trips) and rescued over seventy enslaved people, taking them Northward to Philidelphia and sometimes Canada.
One of her confidants was William Still, who is known today as the “Father of the Underground Railroad”. Still’s parents, Levin and Charity (Sidney), were born as slaves in Caroline County. Their house, if you want to use that generous term, still stands at the Caroline County 4-H park, and I encourage everyone to go visit it. Levin was able to work in his free time and built up enough of a savings to purchase himself from his enslaver, however he knew that he would never get enough cash together to buy his wife and their four children. Charity attempted to escape once with all four children but was caught and returned. The second time she fled, she took with her only her two youngest children- both girls. She probably was not as heavily pursued the second time as her two older sons that she had left behind were of more value to an enslaver. Her and Levin set up a home in New Jersey and had many more children, William being the youngest. As a young man he moved to Philidelphia and became heavily involved with their Anti-Slavery Society, eventually setting up his own house as sort of a landing spot for recently escaped African Americans. If you think of Harriet Tubman as the “boots on the ground” gal, William Still was the logistics coordinator for the Underground Railroad. He kept in touch with those willing to assist as Underground Railroad “stationmasters” and helped to rehabilitate and protect those who successfully arrived at his home. Because he noticed how easy it was for loved ones to be separated by this chaotic system (freedom seekers usually changed their names, and seldom told others they were planning to escape, let alone where they were going), he began to host interviews. He asked those who passed through his living room their names, where they had come from, and where they were going. Curiously, though, he captured something that no one else had bother to think about- narratives about slavery from those who had been through it first hand. His book, “The Underground Railroad”, has become one of the only pieces of literature from the time period which centers African American freedomseekers as the voice of their own experiences. Their stories were influential in educating those in the North about the horrors of slavery and motivating them to join the abolitionist cause.
Another person who did something similar was Frederick Douglass. Born in Talbot County, he was eventually sold to a man in Baltimore to be used as a laborer in a shipyard, where he met his wife Anna Murray of Denton. Once he escaped enslavement, Douglass traveled around the country and even to England to give speeches about his life and experiences of being enslaved. I have to be careful not to give white Northerners too much credit, but it is worthwhile to point out that communication and exposure between the North and South factions of the country was not at all what it is today, and it is entirely plausible that average Northerners had never been told the truth of how brutal slavery was. Again, while Harriet Tubman and other Underground Railroad agents were covertly aiding slaves to freedom, Frederick Douglass was openly and vehemently denouncing slavery.
The Choptank wasn’t just a navigational guide, it was a tool for evading capture and surviving the trek North. Tracking methods were obviously less sophisticated in the 18th an 19th centuries, and freedom seekers could disguise their paths by crossing the river back and forth as necessary to create a dead-end of their footprints. However, many enslaved people could not swim. This meant that areas of more manageable depth, such as Greensboro, became popular crossing points. Plants and fish, provided by the Choptank, most likely became a runaway’s main diet. The water turns from brackish to fresh about two miles South of Denton, meaning that freedom seekers from the Eastern Shore did not have issues with access to water like their more Southern / inland counterparts. Traveling on the water, while more rigorous, was usually faster and safer than traveling on foot.
Moses Viney, an enslaved man from Talbot County, used the Choptank River to his advantage in his escape to freedom.
Moses fled on Easter morning in 1840 to avoid being “sold down the river”. Two of his enslaved friends, Hinson Piney and Washington Brooks, joined him. The three made their way to Denton by following the river on foot. Still, they were being pursued by slave catchers with hounds (many slaveholders had hound dogs on their properties for this very purpose, to become familiar with the scent of the slaves and be able to track them if they escaped). But, Moses expected this. He had spent months leading up to his escape befriending these dogs, and it paid off- the dogs left him unharmed and listened to his command to return home. Upon discovering an abandoned canoe, Moses took the opportunity to get off land and onto the water where he would be inaccessible to the slave catchers who were no doubt close behind. Winey, Piney, and Washington used fence posts as makeshift oars to row the canoe across the Choptank River, evading capture. The trio traveled by night and hid by day until they reached Delaware, where they were able to catch a steamboat to Philadelphia. Moses Viney’s story encapsulates the ability of freedom seekers to use the Choptank as an escape route and resource.
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