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Heritage Trails

Heritage Trails  |  Sites & Landmarks  |  Museums   |  UGRR | Genealogy & Historical Info


Painting by Mark PriestHarriet Tubman Underground Railroad Byway

Freedom seekers found shelter and assistance in Caroline County as they traveled along the Underground Railroad to Delaware. Explore by foot and by car the history and the lore of Harriet Tubman, Frederick Douglass and others. Sites include: Poplar Neck near Preston where Harriet Tubman made her greatest rescues; the Jacob Leverton Dwelling, (privately owned), the only documented Underground Railroad station building remaining on the Eastern Shore of Maryland; the Courthouse Square in Denton, the site of numerous incidents and the jail that held captured freedom seekers and Underground Railroad agents; and Hillsboro, the location of the permanent separation of Frederick Douglass family among various slaveholders. The “Finding a Way to Freedom”  map-guide is available by calling 410.479.0655, or download here.  For more information, visit

Civil War Trail

Civil War history is laced with stories of conflict, intrigue, heroes, and spies. Caroline County boasts six sites on the Maryland Civil War Trail, including: Greensboro, where pro-Union residents sought help from President Lincoln against alleged Rebel arsonists; Denton Wharf, where arrested Southern sympathizers departed by steamboat for imprisonment at Fort McHenry; Caroline County Courthouse, where Unionists rigged the vote that emancipated Maryland slaves in 1864; and the Nanticoke River near Federalsburg, a “smuggler’s paradise” early in the War.

Michener’s Chesapeake Scenic Byway
Coming soon.