Harriet Tubman Underground Railroad Byway
Length: 125.0 mi / 201.2 km
Time to Allow: Take a day or two to explore the byway
The Harriet Tubman Underground Railroad byway traverses a living land-and-waterscape, and commemorates Harriet Tubman and everyone – black and white, enslaved and free – involved in the Underground Railroad. Not a railroad in the true sense, the Underground Railroad was the name given to the secret network of roads, waterways, trails, and hiding places, used before the Civil War by enslaved people fleeing from bondage.
Threading together some of the most pristine and well-preserved working landscapes found along the East Coast, the Harriet Tubman Underground Railroad captures the same culture of family farming and life on the Chesapeake that Tubman grew up in. To explore the byway landscapes is to walk in Tubman’s footsteps as she grew from infant to woman, enslaved to free, ordinary to extraordinary.
You’ll find amenities all along the byway, but it's best to plan ahead. Welcoming towns and hamlets reflect the vernacular architecture of the Chesapeake Bay in the 1850s. In addition to driving the byway, find ample opportunities to hike, bike, paddle, shop, dine, and attend events relating to the area’s significant and unique heritage.
Reliving History on the Harriet Tubman Underground Railroad Byway
Your heart is racing, and you can hear the bay of bloodhounds on your trail. Only the hope of freedom keeps you moving forward. Out of the darkness steps a woman you have heard called Moses, and you know that freedom is within your grasp.
Harriet Tubman earned the name "Moses of Her People" because she helped so many of her fellow slaves to freedom (around 70!) This courageous woman never lost a passenger on the “Underground Railroad," a network of abolitionists and former slaves who helped fleeing slaves gain freedom before the Civil War. Travel along the Harriet Tubman Underground Railroad Byway in Maryland and discover the story of this amazing woman and the cause she represented.
In the byway town of Cambridge, visit the Dorchester County Visitor Center and browse exhibits highlighting Harriet’s life and the Underground Railroad. Pick up the brochure, “Finding a Way to Freedom Driving Tour” (also available online.) This guide includes directions to significant Underground Railroad sites on the byway, as well as tales from the lives of Tubman and other abolitionists. Assistants are on hand to answer any of your questions, making the visitor center the perfect place to plan your trip.
Learn even more about the life of this brave abolitionist at the Harriet Tubman Organization Museum, also in Cambridge. Photographs of Harriet Tubman and other notable African Americans line the walls, as do photos of picturesque Dorchester County landscapes. Join a guided tour of the museum to hear exciting tales of daring escapes via the Underground Railroad. Other museum features include a 30-minute film about the Underground Railroad and a large, colorful mural depicting scenes of Harriet Tubman’s life.
For a look at the landscape of Tubman's early life, go to the byway town of Madison, where many historians believe she was born. The Stewart family, owners of both Harriet and her father Ben Ross, owned a lot of property in this area, including a mill. As you drive through Madison, look for the Stewart Canal. Around 1850, John Stewart had his slaves, along with some free laborers, build a canal from the woods to his mill to transport lumber there more quickly. Imagine slaves digging the canal with simple hand tools under the hot Maryland sun more than 150 years ago.
Mosquitoes swarm around you and worry fills your heart. What lies ahead? Fearful, you turn back, intending to return. Before you can slip away, Moses stands before you, pistol cocked and leveled at your head. “You’ll be free or die,” she says.
Today, you can travel the byway through the nearby Blackwater National Wildlife Refuge in comfort. But in Harriet’s time, this was the kind of terrain that escaping slaves would have had to traverse on foot. Forbidding tidal marshes, water-logged woodlands, and cropland dot the landscape. Unsure of what lay ahead, many slaves wanted to return to their owners. Knowing that even one returning slave would endanger all the others, Harriet Tubman carried a pistol and would threaten to shoot. Explore this terrain firsthand either by land or water. Four trails wind through green forests, near sparkling rivers, and close to marshes. Or, take one of three aquatic trails by canoe or kayak and see the same views from a different perspective.
Harriet’s first act of public defiance was at the Bucktown Village Store in Bucktown, just east of the refuge. In the 1830s, young Harriet Tubman refused to help an angry overseer subdue another slave. Furious, the overseer accidentally hit Harriet in the head, fracturing her skull, an injury that plagued her the rest of her life. The Bucktown Store has been restored to resemble what it would have looked like at this critical point in her life. At the store, you can explore interpretive panels describing the event, or take a guided historical tour of the store.
Want to see an actual safehouse along the Underground Railroad? At the middle of the byway in Preston is the Leverton House and Farm, the main stopping place for the Underground Railroad in the region. White abolitionists Jacob and Hannah Leverton helped many to freedom until they were exposed in 1858. The family then sold their property and moved to Indiana. An interpretive sign at the site tells the story. (The home is private property and not accessible to the public.)
Preston was also the site of two of Harriet Tubman’s most daring rescues. In 1854 and 1857, Harriet risked her life and liberty to help her brothers and elderly parents to freedom. Her parents’ rescue included a risky daytime train ride for the wanted Harriet and a nighttime escape by horse-drawn wagon for her parents. Drive the road past Poplar Neck and imagine this nerve-racking escape. The plantation is private property, but you can literally follow the footsteps of Harriet Tubman by walking along the road that served as a rendezvous for both her brothers and later her parents.
The byway town of Denton played an important role in both slavery and its opposition. Not only was the Caroline County Courthouse Square the site of a slave market in the early 1800s, but years later, the nearby jail housed noted abolitionists and others. In 1858, Underground Railroad conductor Hugh Hazlett was sentenced to an astonishing 44 years in jail for helping slaves escape (he was pardoned in 1864.) Also in Denton is another landmark of the Underground Railroad, the Tuckahoe Neck Quaker Meeting House (privately owned). Hannah Leverton gave her fellow Quakers many a rousing speech here in support of the Underground Railroad. Just across the river is the Choptank River Heritage Center. At the center, you can learn tales of Denton’s occupation by Yankees during the Civil War. In order to cut off transportation between the North and the South, Union soldiers seized the steamboat wharf and railroad line. During a Fourth of July celebration in 1863, they accidentally burnt most of the town to ashes. The plucky townsfolk rebuilt soon after.
You stumble through fields lit only by a fading moon. Ahead a white stone gleams in the dark, marking the border between the slave state of Maryland and the free state of Pennsylvania. A few steps more and you are free!
Crossing the Mason-Dixon line meant freedom to many of the slaves. Originally surveyed to solve a border dispute between the Maryland, Delaware, and Pennsylvania colonies, the Mason-Dixon line later marked the division between the North and South in the Missouri Compromise. Although freedom wasn’t guaranteed beyond the Mason-Dixon line, crossing it was a huge milestone for slaves. At the end of the byway east of Goldsboro lies one of the original stones laid down to mark the Maryland-Delaware section of this historic line.
Travel the Harriet Tubman Underground Railroad Byway, and discover more about the life and times of this incredible visionary as well as many others whose courage and dedication helped many achieve the dream of freedom that founded our nation.
Harriet Tubman Underground Railroad Byway Infomations came from:
U.S. Department of Transportation
Federal Highway Administration