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 ìriggedî the vote that emancipated Maryland slaves in 1864; and the Nanticoke River near Federalsburg, a "smugglerís paradise" early in the War.
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) a member of the National Park Service National Underground Railroad Network to Freedom Program, 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 Douglassí family among various slaveholders.
Brochure/map available, "Finding a Way to Freedom". 410.479.0655
Cycling Trails
Caroline Countyís 120,000 acres of farmland represent more than half of the county's total acreage. This picturesque farm country coupled with woodland, charming rural towns, and flat modern roads with light vehicular traffic have made it a favorite destination for bicycle clubs from as far away as New York. Caroline has a county-wide cycling guide which maps out 11 bicycle routes ranging from 14.5 to 38 mile trails that can be shortened and customized to suit both the weekend and advanced cyclist. In addition to routes, the brochure includes information on places of interest, dining, lodging and camping. Brochure/map available: "Cycling in Caroline County, Maryland"
410.479.0655
Water Trails
A wealth of rivers and bay tributaries make Caroline County a haven for families and individuals seeking adventures on the water. A nearly 80-mile water trail follows the Choptank and Tuckahoe Rivers. This system links more than 15 existing public access points and provides many opportunities to explore and learn about the Chesapeake Bay and its watershed. Brochure/map available for self-guided heritage paddle trips: "Choptank & Tuckahoe River Water Trails Map Guide" at
www.riverheritage.org or 410.479.0655
