Description - Before the Civil War, many enslaved African Americans fled to freedom in the North from Maryland as well as other Southern states. The so-called Underground Railroad was not a true railroad but was the name given the means by which these enslaved people fled from bondage. With great danger to all involved, those enslaved escaped to freedom via a secret network of roads, waterways, trails, and hiding places. They were helped along the way by anti-slavery activists mainly free blacks, but also a few whites and Native Americans. This byway will bring to life the stories of the Underground Railroad and fugitive slaves, or self-liberators such as Dorchester County's Harriet Tubman and Samuel Green who escaped north in the 1850s. From Dorchester County, you will follow a route north through Caroline County where many Maryland abolitionists supported the cause of freedom.
Harriet Tubman was the most famous "conductor," or guide, on the Underground Railroad. Born an enslaved woman in Dorchester County about 1821, she fled to the North in 1849. She returned many times to lead others to freedom. Samuel Green was a free black farmer, Methodist minister, and local Underground Railroad conductor. He was imprisoned in 1857 when local authorities discovered that he had a copy of the anti-slavery novel Uncle Tom's Cabin.
- The Underground Railroad Trail is known for it's Cultural and Historical Attractions.
Directions from : Start your journey in Cambridge, Maryland with visits to several historical sites related to the Underground Railroad on US 50, Pine Street and High Street and others. Take MD-341 south, continuing as it turns into Maple Dam Road. Near Seward turn east onto Greenbrier Road and continue east and north past Bucktown to join up again with U.S. 50 (just east of Cambridge.)
Take U.S. 50 briefly east until MD-16. Turn north onto MD-16 and follow the route along the Choptank River through Preston, Denton, and Greensboro. At Goldsboro turn east onto MD-287. The byway ends on MD-286 just short of the Delaware state line.