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This Black History Month, we honor and celebrate Caroline County’s African American heritage. Here are a few ways to discover the stories of the remarkable individuals who have shaped our nation.


Experience the Harriet Tubman Underground Railroad Byway

Discover the stories of Harriet Tubman and other freedom seekers who risked their lives to escape slavery on Maryland’s Eastern Shore. The Harriet Tubman Underground Railroad Byway is a self-guided driving tour in Caroline and Dorchester counties that takes you to the places where Tubman lived, fled, and returned to repeatedly to free her family and friends.

You can download the byway map and guide or order a hardcopy here. There is also a free audio guide that brings to life the powerful stories of slavery and escape. Listen to the audio guide as you visit the more than 40 sites along the way. Soundtracks include dramatizations, storytelling, and commentary by experts, historians, and local community members.


Learn About Anna Murray Douglass

Born in Caroline County, Anna Murray Douglass was an entrepreneur of means who helped Frederick Douglass escape to freedom. She was born free in Tuckahoe Neck, and he was born enslaved in Talbot County. They would meet for the first time at the city wharves in Baltimore. Following Frederick’s escape, they would later marry in New York, raise a family, and work 40 years together for civil rights and social justice.

Read the story by Don Barker here.

There will also be a special presentation on Anna Murray Douglass at the Museum of Rural Life on April 6th by Celeste-Marie Bernier, author of the forthcoming “Douglass Family Lives: The Anna Murray and Frederick Douglass Family Collected Works and Biography: Book 1-6” and “The Anna Murray and Frederick Douglass Family Selected Writings: A Reader. Find out more here. 


Discover the Historic Black Schools of Caroline County

Through 90 years of racial segregation and funding disparity, black schools in Caroline County were sacred ground in the fight for equal education, democracy, and civil rights. Eight are still standing.

Learn more about these eight schools and follow our Driving Tour of Historic Black Schools in Caroline County here. 

Find a mobile-friendly version of the Driving Tour of Historic Black Schools in Caroline County here. 

This driving tour has been made possible through a partnership with the Caroline County Historical Society and the generous contributions of Don Barker.


Learn about the National Park Service’s Network to Freedom Sites

The National Park Service’s Network to Freedom program commemorates the places and people who shaped the journey to freedom. These sites are documented places where the enslaved escaped from bondage, routes they took, places where they stayed or found assistance, and places where their freedom was tried and tested.

Caroline County is home to numerous Network to Freedom sites, including the William Still Interpretive Centerthe Caroline County Courthouse, and the Jacob and Hannah Leverton Home. Learn more about about the sites here. Please note that not all Network to Freedom sites are open to the public.


Discover the story of Bishop A.W. Wayman from Tuckahoe Neck

Alexander Walker Wayman, the seventh Bishop of the African Methodist Episcopal (AME) Church, was born in Tuckahoe Neck, Caroline County, Maryland. Young Alexander united with the Methodist Episcopal Church in Denton at age 16. Three years later, he left home for Baltimore and joined the new A.M.E. Church. Wayman served the church in Philadelphia, Baltimore, and Washington D.C. before he was elected Bishop in 1864. Read more of the account of Bishop Wayman’s Long Way Home at the Caroline Digital History Project here. 

*Pictured at the top of the page is the James H. Webb Cabin on Grove Road, Preston. James H. Webb, a free African-American farmer, built this hand-hewn log home around 1852 and lived here with his enslaved wife, their four children, and Webb’s father. The family were members of nearby Mount Pleasant Church. The one-room home, with its “potato hole,” open fireplace, and loft accessed by a crude ladder, was built of materials found nearby. It sits on its original ballast-stone foundation from ships that plied the Chesapeake Bay.