The Eastern Shore is a sub-trail of both Booth and Baltimore trails. Frederick Douglass and Harriet Tubman were born in Talbot and Dorchester Counties respectively and mainlines of the Underground Railroad ran through this region.
As with Southern Maryland, the Eastern Shore had its own underground network of Confederate smugglers and spies, who sent supplies and information down along the Chesapeake Bay.
Men from small towns like Cambridge, Easton, and Chestertown fought for the Confederacy and the Union, including African-Americans. Seven regiments of the United States Colored Troops (USCTs) were formed in Maryland. Of the sixteen African-Americans who won the Medal of Honor during the Civil War, five were Marylanders.
From Route 50, I head north along Route 213 through Chestertown towards Elkton and hop on I-95 south. I cross over the Susquehanna River near Port Deposit, where a local Union artillery battery served with distinction at several engagements including Antietam.
Traffic merges onto the Baltimore Beltway, and it dawns on me that my road trip is ending. The nights of pouring over trail maps, strategically plotting my next maneuver are over. I’ve traveled more than 1,000 miles, stopping at nearly all 215 trail sites.
Along Interstate 70 west, home to where my own adventure began, I think about something Skip Koontz said to me. Koontz is a Civil War “living historian” from Hagerstown, who I met along the way. I asked him, “What is the worst part of re-enacting—of ‘living history?’”
Laughing he said, “Sometimes going home after a weekend. Going back to the 21st century is kinda the pits every once and awhile.”
For more information about Maryland Civil War Trails or to obtain trail maps, visit www.mdwelcome.org or call 1-888-248-4597. For more information about the entire Civil War Trails program visit www.civilwartrails.org .



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