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One of the many free Black people living in Caroline County Tubman wasn’t the only one working to free Caroline and

in the pre-Civil War era was James H. Webb. His log cabin, Dorchester’s enslaved community. The Quaker Leverton
which he built in 1852, still stands outside of Preston. He family, along with a free African American man named
lived there with his father, wife, and four children. Webb’s Daniel Hubbard, operated in Caroline County, guiding
home, which is no larger than a studio apartment, is used freedom seekers through the area to safety. Th e Levertons’
today as an educational tool to represent the lives of free home in Preston, MD near Lincester Mill, served as an

Black Eastern Shore dwellers. Despite the large free Black Underground Railroad “station.” The Choptank River and
population, discriminatory laws, unfair hiring and payment its tributaries made Caroline prime real estate for grist and
practices, disenfranchisement, and other hurdles caused sawmills, places where free and enslaved people would
by government-sanctioned racism prevented them from have worked side by side, where they were able to share

climbing the social and financial ladder. James’ wife, Mary information and resources concerning escape.
Ann, was enslaved.
The Choptank River stands as a powerful symbol of both

Marriage between free and enslaved Black people was oppression and resilience in Maryland’s history. Its waters,
common. Whites encouraged their slaves to marry, as once instrumental in sustaining the brutal institution of
marriage meant procreation, and procreation meant more slavery through the transportation of enslaved Africans
people to treat as property. Over time, this system backfi red and the cultivation of cash crops, later became pathways to
on pro-slavery whites in the Eastern Shore region. There is a freedom for many seeking freedom. In more ways than one,

theory that the reason that two of American history’s most the Choptank River was a tool for self-liberation, as freedom
celebrated freedom-seekers, Harriet Tubman and Frederick seekers used it to navigate Northward and into Delaware.
Douglass, were from the Eastern Shore was due to this Using its shores for evading capture, its plentiful resources for
prolonged exposure to free African Americans. Th ey saw food and herbal remedies, and the network of sympathetic
firsthand that Black freedom could be achieved, and they individuals for shelter and guidance, the Choptank River

wanted it for themselves. Harriet Tubman’s fi rst husband, that once carried their ancestors to their dismal fate proved
John Tubman, was a free man, although he detested her essential for those seeking to free themselves of bondage.
freeing other enslaved people.
Believe it or not, this is just the tip of the iceberg to my full
research on this topic. To read the full version of this article,
complete with personal narratives, the details of the slave
trade in Caroline County, and more in-depth historical
analysis, visit my website at The River is the Center (https://

kthomason1209.wixsite.com/the-river-is-the-cen). I also lead
History on the Choptank historical river cruises. For tickets,

visit my website or find River City Cruise Co. on Facebook.

Locally built, new construction PADDLE
BOARDS and KAYAKS. Paddles included.

Paddle Boards $500 • Kayaks $600
Call 410-490-5560 for info.

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