Harriet Tubman Underground Railroad Byway
Finding a Way to Freedom
| Departure: | Dorchester County Visitors’ Center, Maryland |
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| Destination: | Mason and Dixon Line, Maryland |
| Time to allow: | 3 days |
Before the Civil War, enslaved people in this region used a network of agents, stations, and conductors to reach freedom. The iconic figure for this Underground Railroad was Harriet Tubman, who rescued more than 70 people. Follow the Harriet Tubman Underground Railroad byway from south to north, the direction fugitives on the railroad would have moved, and encounter stories and sites that will help you appreciate the dangers Tubman and all those who “took their freedom” faced.
Each season offers a different, yet meaningful perspective on the byway, so enjoy this tour year round. Just plan and call ahead to ensure that sites are open and that tour guides are available.
Day 1
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Start: Dorchester County Visitors’ Center
Freedom-seeking fugitives on the Underground Railroad traveled from south to north, so begin your byway travels at a southern entrance to the byway, the Dorchester County Visitors' Center. Access the center from either direction on U.S. Route 50, the primary access route to this region.
While you're at the Visitors' Center, look over meaningful exhibits and talk to helpful staff members to gain a background on the byway’s history and culture. An understanding of the region's history will help you appreciate the landscapes you will soon see in the context of the Underground Railroad.
If you plan on taking a guided tour of any of the upcoming stopping points, feel free to ask the staff members here to help you make appointments, and be sure to double-check site hours. In May, pick up promotional materials, suggested itineraries, and maps for the county-wide Heart of Chesapeake Country Heritage Days. Regardless of when you come, be sure to grab a walking-tour brochure of Cambridge’s historic district to complement your next stop along the byway.
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Overnight Point: Historic Cambridge
Directions from previous place: Head south on Rosehill Place/Rose Hill Drive toward Byrn Street. Turn west on Byrn Street. Follow Byrn Street until it turns south into Maryland Avenue, which soon becomes Market Street. Continue on Market Street, turning north on Academy Street, which you'll follow curving west on Spring Street. Follow until you reach High Street in Historic Cambridge.
Distance from Previous Site: 1 miles / 1.6 km Travel Time from Previous Site: 3 minutes As you drive from the Visitors’ Center to the heart of Cambridge, which was settled by whites, free blacks, and enslaved Africans in 1669, notice the unusual “cowpath”-style street pattern. These meandering streets are a legacy of the Dorchester County seat’s 17th-century founding (before the example of William Penn’s city plans led others to impose the more familiar grid pattern visible beyond the heart of Cambridge).
As a seaport community on the lower Choptank River (only a short sail away from the busy Chesapeake Bay), Cambridge has long been a commercial and industrial heart of this region. You can explore the city’s rich maritime heritage in museums, through historic district tours, and on river cruises sprinkled throughout the city. Learn about the bleaker aspect of Cambridge’s past when enslaved men and women were brought here from the Caribbean, the Ivory Coast and other regions of western Africa, and other American seaports. Park on the street near the 1854 Dorchester County Courthouse on High Street, which was once near the town’s slave market, and enjoy the northern end of Cambridge on foot. The present building was designed by the great 19th-century architect Richard Upjohn and was built in 1854. It is one of the few on the Eastern Shore that dates to the time of the Underground Railroad. Look over the outdoor interpretive sign on the grounds to learn about Harriet Tubman’s first rescue, of her niece Kessiah, who was to be sold on the courthouse steps in 1850.
Stroll over to the nearby Waugh Methodist Episcopal Church on 429 High St., and take in one of the oldest African-American congregations on the Eastern Shore. Continue north along High Street to the high-style residential neighborhood built with the funds of wealthy sea captains and merchants at the hands of enslaved and free craftsmen.
Walk two blocks north to see the waterfront park and a modern skipjack, the Nathan. This is the kind of small vessel on which enslaved and free mariners worked as seamen and fishermen from the 18th century onward. The Nathan is a wide shallow-draft workboat with a distinctive large triangular sail (to capture the gentle Chesapeake winds). Skipjacks were invented in the late 19th century as the nation’s craze for oysters mounted. Walking in the opposite direction will take you to a shipyard on Hayward Street-- check it out to see a modern example of the kind of place where many enslaved and free craftsmen worked.
Head south along High Street to reach the Harriet Tubman Organization’s headquarters, in the Pine Street commercial area. First settled by free blacks in the early 1800s, this was once a thriving commercial and arts/entertainment district in the era of segregation. Today, efforts are being made to bring back the rich cultural legacy of this neighborhood. Take part in those efforts by swinging by the annual May Jazz and Blues Festival.
From the Pine Street area, follow Race Street (which led to the mill that once stood on Mill Street near the courthouse) to your next stop, at the heart of the commercial area where a Main Street program and a lively arts community have brought new life to Cambridge’s primary business district. Choose from numerous dining options, fulfill your shopping desires, and find a place to spend the night so you’re rested for another day of byway adventures.
Total Distance Traveled in Day 1: 1 miles / 1.6 km
Day 2
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Stop 1: Harriet Tubman Organization Museum
Directions from previous place: Head southwest on High Street, turning southeast on Poplar Street. Continue on to Race Street. The museum will be on the east side of the street.
Distance from Previous Site: 1 miles / 1.6 km Travel Time from Previous Site: 5 minutes Suggested Time at This Site: 30 minutes Dedicated to the memory of Harriet Tubman, the museum offers memorials, history interpretations, and tours of the museum and Tubman sites. During your visit, you will see exhibits and talk with guides, who are also available to provide tours that follow this itinerary and others. Visit the gift shop for souvenirs that will evidence your byway experience.
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Stop 2: Madison
Directions from previous place: Head south on Race Street. Turn right at Cambridge Beltway/MD-16. Continue to follow MD-16 to the bridge crossing over the canal.
Distance from Previous Site: 13.8 miles / 22.1 km Travel Time from Previous Site: 29 minutes Suggested Time at This Site: 1 hour Here in Madison at Joseph Stewart’s Canal, you can gain a greater understanding of the brutal work required of African-American slave laborers when you contemplate the six-mile, hand-dug canal in the Maryland marshes. Look out over the scenic canal, which was used to transport timber cut from surrounding forested swamps. While it might be scenic today, the canal presented its constructors with the challenging conditions of a steamy summer climate, malaria-carrying mosquitoes, poisonous snakes, and other pests.
As you drive the length of the canal, you’ll pass the Stanley Institute, which was built after the Civil War. Not far from the institute, a mass escape of slaves called a “stampede” took place in 1857. Continue to follow the byway to the Madison shipyards, which were the destinations of the timbers delivered by the canal. Here, Harriet Tubman and her father frequently worked and visited.
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Stop 3: Blackwater National Wildlife Refuge
Directions from previous place: Turn around and head east on MD-16/Taylors Island Road. Turn south when you reach Golden Hill Road/MD-335 to reach the Blackwater National Wildlife Refuge.
Distance from Previous Site: 11.9 miles / 19.0 km Travel Time from Previous Site: 24 minutes Suggested Time at This Site: 2 hours Get a taste of the dramatic Blackwater National Wildlife Refuge (BNWR) scenery as you drive to the visitor center. Take in this vast, remote wildness and consider the skills required to stay alive, much less navigate this terrain. You can imagine how a sense of direction, knowledge of wildlife and foraging, and constant vigilance would have been critical to fugitives seeking freedom through this landscape.
When you reach the BNWR visitor center, pick up some travel information, witness an osprey nest through the “osprey cam,” and learn about the rich natural resources of this special place through the exhibits.
For a closer look at the surrounding forests and wetlands, push off in a kayak or canoe on one of the refuge’s four paddling trails or choose among five short walking trails. On the 1.7-mile Tubman Road Trail, you’ll find interpretation and likely catch a glimpse of the many amphibians, some rare, found in this landscape.
Drivers, cyclists, and pedestrians can also enjoy the Wildlife Drive, a four-mile paved road along the Blackwater River. Bring your camera-- waterfowl, shorebirds, turtles, deer, endangered Delmarva fox squirrels, ospreys, and Bald Eagles all reside here.
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Stop 4: Bucktown Village and Store
Directions from previous place: Head east on Key Wallace Drive, turning north on Greenbrier Road. Continue until you reach the intersection with Bestpitch Ferry Road.
Distance from Previous Site: 5.4 miles / 8.6 km Travel Time from Previous Site: 11 minutes Suggested Time at This Site: 30 minutes When you reach Bucktown, you’ve reached the heart of “Harriet Tubman country.” This area has been historically recognized as Harriet Tubman’s birthplace even though there is no conclusive evidence as to the exact birth site of 1822. Tubman did spend her early years working here and on nearby farms some of which are much the same today. Tubman made her escape from the Thompson farm. Park your car at the pullout here to look over the interpretive marker and pay homage to Tubman in her home town.
As you drive, don’t overlook the quaint yellow building at the intersection of Greenbrier and Bestpitch Ferry Road-- the Bucktown Store is a key site in Harriet’s life experience. History tells how, as a 13-year-old girl visiting the store, Tubman blocked an overseer’s effort to discipline a fellow slave. In his frustration, the overseer struck Tubman in the head with a 2-pound block of iron. She nearly died from the injury, and it left her prone to sudden seizures and spiritual visions the rest of her long life. Her survival after such an injury indicates the physical toughness that enabled Tubman to play the role of Underground Railroad conductor.
Although it is disputed whether this is the actual building from Tubman’s time, it hails from the mid-19th century and occupies a traditional location in the landscape. The owner of the store is a descendant of generations of owners and residents of this area, and if you call ahead, you can tour the store and landmark in Harriet’s life.
Also in Bucktown, you can visit Scott’s Chapel or the Bucktown United Methodist Church. Tubman and her family may have worshiped with this congregation, since services would have been easy walking-distance from her home. Though integrated in its early years, the graves are segregated. You are welcome to worship on Sunday mornings or Wednesday evenings, or to visit the grounds at any time.
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Stop 5: East New Market National Historic District
Directions from previous place: Head north along Bestpitch Ferry Road toward Greenbrier Road and the intersection with Bucktown Road. Continue northeast on Bucktown Road. Turn east onto Cordtown Road. Turn east again at Aireys Spur Road. When you reach MD-16/Ocean Gateway/US-50, turn east. Travel east turning north onto MD-16/Mount Holly Road/Mount Holly East New Market Road. East New Market lies along MD-16 at its intersection with MD-14.
Distance from Previous Site: 14.6 miles / 23.4 km Travel Time from Previous Site: 32 minutes Suggested Time at This Site: 45 minutes From Bucktown to East New Market, you’ll follow an old Indian trail paralleling the Choptank River through a beautiful area of large, prosperous farms sweeping back to a forested treeline. When you arrive in East New Market, stretch your legs by walking around the town’s charming historic district on a self-guided walking tour. You’ll enjoy excellent examples of colonial and early American architecture and a town that a visitor from the 19th century would readily recognize.
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Stop 6: Leverton House and Farm
Directions from previous place: Head west on MD-14/E New Market Rhodesdale Rd. Turn north on Main St/MD-16/E New Market Elwood Rd. Turn northwest at MD-16/MD-331/Preston Rd. Then turn east on Seaman Rd. Head south on Seaman Rd toward Langrell Rd. Turn right at MD-16/MD-331/Preston Rd 7. Turn east at Linchester Rd., and you will find the mill and parking on the east side.
Distance from Previous Site: 8.2 miles / 13.1 km Travel Time from Previous Site: 19 minutes Suggested Time at This Site: 1 hour After parking at the mill, walk to the “the main stopping place for the Underground Railroad in the region,” the Hannah and Jacob Leverton dwelling. This brick house not far upstream from the mill on Hunting Creek belonged to Jacob and Hannah Leverton, white Quaker abolitionists. Their son Arthur W. Leverton and their neighbor Daniel Hubbard were exposed in 1858 as agents of the Underground Railroad. The family fled to Philadelphia, but the site is listed in the National Park Service’s National Network to Freedom for this family’s activities. If you have half an hour to spare, walk to the entrance and take a snapshot of this property where Harriet Tubman might have found assistance during her escape.
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Stop 7: Choptank Village and Choptank River
Directions from previous place: Head northwest on Linchester Road through the remainder of Linchester Village. Turn toward Main Street/MD-16/ MD-331/Preston Road (follow one-way direction). Turn east at Main Street/MD-16/MD-331/Preston Road. Turn southwest at Maple Avenue and continue on Choptank Road. (Note, leaving Choptank for Poplar Neck, the bridge mapped over Marsh Creek using Poplar Neck Road is permanently closed.)
Distance from Previous Site: 4.2 miles / 6.7 km Travel Time from Previous Site: 12 minutes Suggested Time at This Site: 30 minutes This tiny river town, known in 1855 as Leonard’s Wharf, was a port and steamboat landing for the town of Preston. Little has changed since the 19th century. The landing and harbor, still in use, was the scene of at least one documented escape, where freedom-seekers, possibly the Dover Eight, were escorted upriver to Tubman’s parents’ home on Poplar Neck.
You’ll be grateful for a camera here; the village affords the best view of the Choptank River this far north until Denton. If you’d like to explore these waters, which served many fugitives in their escape, then pick up a paddle and take to the water trail by boat from the public boat landing.
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Stop 8: Poplar Neck
Directions from previous place: Head northeast on Choptank Road. Turn west at Havercamp Road. Turn at Poplar Neck Road, turn around after 1.6 miles. (Note, the bridge mapped over Marsh Creek, using Poplar Neck Road to enter Choptank, is permanently closed.)
Distance from Previous Site: 4.2 miles / 6.7 km Travel Time from Previous Site: 12 minutes Suggested Time at This Site: 30 minutes Poplar Neck is a typical mid-19th century farmstead that was home to the Thompson family and their slaves, including Ben Ross, Harriet Tubman’s father. Tubman’s parents moved here in 1847 and were active in the Underground Railroad. When they were exposed in 1857, she helped them make a dramatic escape to Canada. On Christmas Day 1854, she returned to help her brothers escape. Evidence points to this being the location where Tubman may have liberated herself in 1849.
See the privately owned farmstead from the access road or from the seat of a kayak on the Choptank River.
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Stop 9: James Webb Cabin
Directions from previous place: Head north on Poplar Neck Road. Turn east at Marsh Creek Road. Continue on Sunset Boulevard until you reach Main Street/MD-331. Travel Main Street, turning northeast at Harmony Road/MD-16. Turn north at Grove Rd. The log cabin is on the west side.
Distance from Previous Site: 7.8 miles / 12.5 km Travel Time from Previous Site: 19 minutes Suggested Time at This Site: 15 minutes Visit the one-room James Webb log cabin with its “potato hole,” open fireplace, and loft accessed by a crude ladder, built circa 1857 by a free black man. The cabin stands near Harriet Tubman’s possible Underground Railroad route from Poplar Neck and represents the kind of housing that sheltered many African Americans in the mid 19th century. Enter this home, and get a feel for the conditions enslaved and poor people in this region endured.
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Overnight Point: Historic Denton and Courthouse Square
Directions from previous place: Head west on Grove Road. Turn north east at Bethlehem Harmony Road/MD-578, which becomes Harmony Road. Turn north at Denton Bridgeville Road/MD-313/MD-404. Continue to follow MD-404. Turn west at Hillsboro Denton Road/MD-404. Continue on Market Street. Use on-street parking.
Distance from Previous Site: 16.4 miles / 26.2 km Travel Time from Previous Site: 34 minutes Park on the street in front of the Caroline County courthouse, site of a slave market and jail that held fugitive slaves and Underground Railroad operators. Walk to the attractive, small building on the corner of the courthouse grounds to find traveler information.
Continue only a short block from this kiosk to a Civil War Trail marker in front of the Museum of Rural Life, which raises the story of a possible vote fraud that led to the narrow passage of a bill in the Maryland state legislature emancipating Maryland’s slaves in 1864. Go inside the museum to discover something about the Underground Railroad and local African Americans in Caroline County. Peruse exhibits on the county’s three centuries of agricultural economy and displays demonstrating the contrasting housing styles from the period.
Of course the museum is one structure along the courthouse square, which is faced on all sides by noteworthy residences and commercial structures dating from the mid 19th through early 20th centuries. Stroll five minutes away across the Choptank River to the Choptank River Heritage Center. Enter the center if you made an appointment, or explore the grounds and the wharf extending from the replica steamboat offices at anytime. From the Center’s exhibits you’ll learn about the maritime commerce of the Choptank River, a busy inland waterway that was both challenge and opportunity for fugitives.
Like Cambridge, Denton was a regional market center for the Eastern Shore, further inland. Take some time to enjoy Denton’s Main Street and surrounding blocks. Stop at a restaurant or visit a coffee house within comfortable walking distance before retiring for the night at a local hotel.
Total Distance Traveled in Day 2: 87.5 miles / 140.0 km
Day 3
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Stop 1: Atkins Arboretum at Tuckahoe State Park
Directions from previous place: Head northwest on Market St toward N 1st St. Turn west at Gay Street/MD-404. Turn west again at Hillsboro Denton Road/MD-404. Turn north at MD-480/Ridgely Road. Head north at Eveland Road. to reach the park.
Distance from Previous Site: 8.6 miles / 13.8 km Travel Time from Previous Site: 20 minutes Suggested Time at This Site: 2 hours 30 minutes On your byway tour, you have seen the extensive marshes of the lower Chesapeake Bay that begin in Dorchester with the Blackwater National Wildlife Refuge as well as the wooded tidal wetlands at Linchester Mill. Here at Adkins Arboretum you’ll see other kinds of habitat through which fugitives of the Underground Railroad had to pass. Freshwater wetlands, meadows, and mature forests of mixed hardwoods--poplar, sweet gum, oak, and hickory--paint the scene at Tuckahoe State Park. At the Arboretum, you’ll see native plant species that have evolved on the Delmarva Peninsula over hundreds to thousands of years and today provide food and shelter for the area wildlife. Stop at the visitors’ center and listen to an audio tour with 35 stops. You can also go on a guided walk if you prefer a more personal approach to explore this lush arboretum.
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End: Mason and Dixon Line
Directions from previous place: Head south on Eveland Road. Turn south onto Ridgely Road/MD. Then turn west onto Shore Highway/MD 404. Take the MD-313/MD-619 ramp toward Denton/Greensboro. Turn north onto MD-313/N 6th Street. Continue to follow MD-313. Keep north onto 311. Turn east onto Sandtown Road/287 East. Turn south onto Bright Road. Turn right on Draper’s Mill Road. Turn left onto Lords Corner Road, where you'll find a Mason and Dixon crownstone.
Distance from Previous Site: 22.8 miles / 36.5 km Travel Time from Previous Site: 30 minutes When you reach the Mason and Dixon line after your journey, you can imagine how an enslaved person must have felt crossing the line into the north, both emotionally and legally. Take a photo of the crownstone, one of many along the boundary between the north and south, free and slave, to mark the end of your journey.
