1. Dorchester County Visitor Center

Information and Orientation for the Journey

Overlooking the Choptank River, the Dorchester County Visitor Center is the perfect place to begin your byway adventure. Inside the center, an exhibit provides background information on Harriet Tubman and Underground Railroad activity in the area. Knowledgeable staff can assist you in planning your tour and will provide information on events, accommodations, dining opportunities, shopping, and outdoor experiences.

In 1608, English Captain John Smith met Native Americans here when he explored the Chesapeake Bay. As the colony flourished, so did demand for cheap labor. In 1664, the General Assembly codified a system of slavery that for 200 years supported an economy based on the labor of enslaved workers. In time, Dorchester’s proximity to free states made it a hotbed of Underground Railroad activity, until emancipation came to Maryland slaves at the end of the Civil War in 1864.

Please visit the Dorchester County Office of Tourism’s website at VisitDorchester.org to learn how to make the most of your time while in Dorchester County, including information on local lodging, dining, events, history, shopping and more.

2. Harriet Tubman Memorial Garden

Honoring Harriet Tubman

Relatives of Harriet Ross Tubman still live in Dorchester County as do descendants of the enslaved and slave holders. Members of the local community chose to honor Tubman at this quiet roadside garden. People across the country can join them in paying their respects to this American hero.

Tubman’s story, that of a young slave who freed herself, then returned to rescue family and friends, inspires emotional and artistic expression in works of literature, music, sculpture, paint, and performance. One of Tubman’s relatives, Charles Ross, painted the murals here. Exterior exhibits describe her life and Underground Railroad activities in the area. The Memorial Garden is located adjacent to Route 50 East, near a variety of accommodations and services.

5. Long Wharf

Portal to Slavery – Gateway to Freedom

In the 18th century, when people, goods and information traveled by water, Cambridge was a regional center for the slave trade. Ships from Africa and the West Indies brought kidnapped Africans and sold them along this waterfront until the trans-Atlantic slave trade was outlawed in 1808. Soon, southern states began cultivating cotton, increasing their need for enslaved labor. About the same time, wheat prices plummeted causing a surge in the sales of enslaved people from the Eastern Shore. Thousands of them were eventually shipped from this wharf to plantations in the Deep South, never to see their homes or families again.

7. Stanley Institute

School of Determination

During a three week period in October 1857, 44 enslaved people in two large groups successfully escaped from farms near here and in Cambridge. Five families – the Vineys, Anthonys, Cornishes, Ambys, and Hills –- carried 20 children with them. Heavily armed, the freedom seekers were determined to avoid capture by bounty hunters. Almost caught near Wilmington, Delaware, the freedom seekers reached Philadelphia and then Canada with the help of black and white Underground Railroad agents.

National newspapers called the escapes a “Stampede of Slaves.” Sadly, some of these self-liberators were forced to leave loved ones behind. The story of the Underground Railroad is not always one of triumph and liberty, but rather, it is also the story of the people who could not or would not leave, and those who were left behind.

Before the Civil War, it was a crime to teach a slave to read, and there were few opportunities to learn. In 1867, this oneroom schoolhouse was moved here. The Rock School, now called the Stanley Institute, is an early example of a post-Civil War African-American school built and run independently by the local black community. It stands as a testament to the black community’s determination to educate their children in a segregated school system. This school was used until the 1960s. The Christ Rock Church, across the street, was built in 1875.

8. Church Creek

Crosscurrents of Slavery and Freedom

Church Creek was a thriving shipbuilding center on the waterfront during the 1830s. Workers in the maritime trades – shipwrights, caulkers, sail makers and blacksmiths – labored and mingled at the wharves with highly mobile, free black sailors. These “Black Jacks” were part of a secret communication network that spanned not only coastal American towns, but also across the Atlantic. They brought news, ideas, and information to enslaved communities, spreading notions of liberty and equality, as well as gossip. Sometimes they provided a means to escape. In the early 19th century, a large community of enslaved and free black families lived and worked between here, Harrisville and White Marsh Roads.

Church Creek sits along Route 16, which follows an ancient pre-colonial Indian trail used for seasonal migrations and trade between the Chesapeake and Delaware bays. “The great majority of enslaved people who fled this county before the Civil War came from places along this road, which begins in Taylors Island to the west and continues northeast through Cambridge. The freedom seekers followed the direction of this route and headed into Caroline County, Maryland and onto Delaware.” Access to information and escapes via vessels likely secured this route’s reputation as a “Highway to Freedom.”

9. Malone’s Church

Early Church

For decades before the Civil War, four nearby communities, connected by footpaths through the woods, provided a strong social network among free and enslaved blacks. As soon as the war ended, these communities established their own African American churches. Founded in 1864, Malone’s Methodist Episcopal Church was the first. Their immediate formation after emancipation indicates that strong faith communities existed long before freedom came.

Beginning in the 1790s, a small but growing free black community established itself on lands surrounding this church. Over the years, more free families settled this area between Harrisville and White Marsh roads, known as Peter’s Neck. Many intermarried with enslaved families held in bondage by the local white landowners. This community created an important social world for Harriet and her family. The people timbered the land, farmed and worked the docks in nearby Madison.

Araminta Ross or “Minty,” later known as Harriet Tubman, was probably born in 1822 at Anthony Thompson’s farm on nearby Harrisville Road. Thompson cultivated grains and other foodstuffs, but timbering the white oak, pine, walnut and maple on his lands occupied the majority of his enslaved people’s efforts. By the time Harriet was born, Thompson enslaved nearly 40 people, including Ben Ross, her father. Ben was one of Thompson’s most valuable men. As a timber cutter and inspector, Ben’s skills increased the profitability of Thompson’s lands.

Tubman’s mother, Rit belonged to Thompson’s stepson, Edward Brodess, who later moved Rit and five of her children, including young Araminta (Harriet Tubman), to his farm in Bucktown. By 1840, Rit, Tubman, and several siblings were back living on Thompson’s farm. Harriet Tubman’s birth site is on private property. Nearly 200 years after her birth, no structural evidence of slave quarters remains at the site. Oral tradition suggests that Harriet Tubman worked and lived near the historic Malone’s Methodist Episcopal Church with her free husband, John Tubman.

10. Madison

Roots of Family and Community

Harriet Tubman spent her formative years around Madison. After living in Bucktown as a young child and adolescent, teenaged Harriet Tubman was hired out to work for John T. Stewart, who owned farms, a shipyard and businesses here. She toiled in the Stewarts’ house (no longer standing), then in their fields, on the docks and in their timber business.

Working for the Stewarts brought Harriet back near the community where her father lived and where she had been born. Tubman’s father, Ben Ross, was set free in 1840, and he worked in Stewart’s lumbering operation. Harriet learned important outdoor survival skills while laboring with her father in the woods, such as how to navigate by the stars, and find food and fresh water. These skills later proved vital as she confidently guided passengers along the Underground Railroad to freedom.

Harriet Tubman successfully led away Winnebar Johnson, enslaved by Samuel Harrington, from here in early June 1854. Johnson later passed through Underground Railroad agent William Still’s office in Philadelphia, where Still noted that Johnson had been “brought away by his sister Harriet two weeks ago.” Johnson was passed along to the bustling port of New Bedford in Massachusetts, where he lived and worked with other freedom seekers, some from Dorchester County.

In December 1854, Tubman had a coded letter sent to Jacob Jackson, a free black farmer who lived west of Madison. The postmaster read the letter and confronted Jackson, who denied knowing what it meant. But Jackson quickly notified Tubman’s brothers that she planned to lead them north from their parents’ home at Poplar Neck in Caroline County. When Harriet Tubman’s three brothers made it to freedom in Philadelphia, they chose as their aliases: James Stewart, John Stewart, and William Henry Stewart – the names of the white Stewart brothers.

11. Joseph Stewart’s Canal

Danger and Drudgery in the Marshes

Drive-by Access Only

Over a period of 20 years, 1810-1832, enslaved and free blacks dug this seven-mile canal through the marsh by hand. It was a grueling and sometimes deadly endeavor. The wealthy, powerful, and slave-holding Stewart family owned large tracts of timber, shipyards, a store, and a mill near here. Joseph Stewart, Anthony Thompson, and nearby landowners designed this canal to float their logs and agricultural products to the ships at nearby wharves in Madison Bay.

Through her work on the docks and in the forests, Harriet learned the secret networks of communication that were the provenance of African-American men, particularly those employed as mariners, carrying timber and other goods to cities and towns around the Chesapeake Bay and into Delaware, Pennsylvania and New England. Beyond the watchful eye of white masters, they spoke of freedom in the North, the safe places along the way and the dangers in between. Feeding her own growing resentment of slavery’s injustices, the free world beyond the shores of Dorchester County emboldened Harriet.

In December 1854, after she had escaped to the north, Tubman communicated to her three brothers through Jacob Jackson, a Madison resident and free black veterinarian. Hearing through the secret maritime communication network that her brothers were about to be sold, she let Jackson know through a coded letter that she was ready to rescue them. Jackson lived south of this canal, and his former home site is now protected as part of the Harriet Tubman Underground Railroad National Historical Park.

12. New Revived United Methodist Church

The New Revived United Methodist Church, once known as Jefferson Methodist Episcopal Church, was established in Smithville in 1876. Before the Civil War, Methodist Camp Meetings were popular in the area.

Following the Civil War, four African-American churches, including this one, were built in nearby local communities. In1864, Malone Methodist Episcopal Church on White Marsh Road was the first to be established, followed by Christ Rock Methodist Episcopal Church near Cambridge in 1875, then Jefferson Methodist Episcopal Church here in 1876, and St. Paul’s United Methodist Church in Harrisville in 1880.

One by one, the churches closed their doors following World War II as families moved away and the number of congregants declined. Today, people from each of these four congregations are part of the New Revived United Methodist Church congregation. Harriet Tubman’s brother, William Henry Ross Stewart, married Harriet
Parker, a free woman from Smithville, around 1850. In late 1854, Harriet Tubman helped three of her brothers escape to Canada, including William Henry. His wife joined him with their two small children in 1855. Marriages between members of these neighboring communities illustrate the social interaction between free and enslaved people before the end of the Civil War and emancipation.

13. Buttons Creek

The Art of Disguise

Jane Kane was enslaved by Horatio Jones, whom she described as “the worst man in the country.” Jones’ plantation sat along Buttons Creek and the Blackwater River, west of this landing on property that is now part of the Blackwater National Wildlife Refuge. Harriet Tubman’s brother, Ben Ross, had hoped to marry Jane, but Jones refused to allow them to do so. Ben arranged for Jane to join him when he and his brothers planned to flee during the Christmas holidays in 1854.

Just before the escape, Ben hid a suit of men’s clothing in one of Jones’ gardens. On Christmas Eve, Jane put on the clothes and slipped quietly away from the plantation. Though she was soon discovered missing, the other slaves on the farm failed to recognize that the “young man” walking up from the garden, “as if from the river,” was actually Jane. Cleverly disguised in men’s clothing, she successfully executed a daring plan to flee her heartless master. She was soon on her way to be with Ben and to secretly rendezvous with Harriet Tubman at Poplar Neck in Caroline County.

This site can be viewed by canoe, kayak or small boat on one of the Blackwater National Wildlife Refuge’s water trails. Stop at the boat launch on Route 335 near the state park.

14. Harriet Tubman Underground Railroad Visitor Center

Honoring a Hero

The Harriet Tubman Underground Railroad Visitor Center is open Tuesday-Sunday, 10am-4pm. Closed Monday. No reservations needed.

The Harriet Tubman Underground Railroad Visitor Center is located amid the landscapes where Tubman lived and toiled. The unspoiled scenes in the area look much as they would have in Tubman’s time. The Tubman Visitor Center features 10,000 square feet of engaging, enlightening multimedia exhibits about her life. It’s a great stop itself and a great launching point for exploring the Harriet Tubman Underground Railroad Byway, a scenic, self-guided driving tour that includes 36 sites related to Tubman and the Underground Railroad on Maryland’s Eastern Shore, with more sites in Delaware leading to Philadelphia.

The visitor center is open 10am-4pm, Tuesday through Sunday. No reservations needed. Admission is free, but donations are welcome.

Exhibits feature information about Tubman’s childhood and young adulthood, living and laboring under slavery here in Dorchester County and neighboring Caroline County. The center immerses visitors in the secret networks of the Underground Railroad and Tubman’s own daring rescue missions. Exhibits also feature Tubman’s actions during the Civil War, and her later years as a suffragist, civil rights worker and humanitarian. The exhibits emphasize her values of faith, family, community, and freedom. Tubman’s story is still relevant today, transcending race, gender, age, religion, and nationality — and shows us that regardless of circumstances, you can make choices that positively impact others.

The 10,000-square-foot visitor center includes exhibits as well as a theater that tell the stories of Harriet Tubman’s life and work. It also includes a classroom, gift shop, and library. If you’re bringing children, be sure to stop by the front desk and ask about the Junior Ranger program. The state park’s 17 acres include a meditation garden, nature trails and a 2,600-square-foot outdoor pavilion (for gatherings of no more than 75 people) available by rental (email htursp.dnr@maryland.gov for details). The center includes state-of-the-art green elements such as bioretention ponds, rain barrels and vegetative roofs.

To request a tour for a group, complete the tour request form.

The Harriet Tubman Underground Railroad Visitor Center is operated by the Maryland Park Service in partnership with the National Park Service to honor Harriet Tubman. It opened to the public in March 2017. For more information, go to the Tubman Visitor Center website.

15. Blackwater National Wildlife Refuge

Timeless Landscapes

COVID-19 UPDATES:

• The Blackwater Visitor Center is open Tuesday through Sunday, 10am to 4pm.
• The Wildlife Drive and refuge trails are open daily from sunrise to sunset.

The forests, marshes, and waterways that characterize the 30,000-acre refuge are largely unchanged from the time that Harriet Tubman lived and worked in Dorchester County. The refuge is situated halfway between where she spent portions of her childhood on Edward Brodess’ farm near Bucktown and the plantation where her father labored and where she was born at Peter’s Neck. Knowledge of the terrain was vital to survival while hiding and trying to flee.

Tubman and others had to successfully navigate the land and waterways, trap and forage for food, and hide from their pursuers. Fleeing slaves often lacked proper clothing to protect them from the elements and they suffered from weather extremes and insects, in addition to the terror of drowning or being caught. Though Harriet Tubman is not known to have liberated others from this area, several escapes did occur within the refuge boundaries.

The Blackwater Visitor Center is open 10am to 4pm, Tuesday through Sunday; closed on Thanksgiving and Christmas. For more information, visit fws.gov/blackwater, or call 410-228-2677.

16. Little Blackwater Bridge

At work in the marshes

A bridge has crossed the Little Blackwater near here since the 1700s, when Harriet Tubman’s grandmother, Modesty, was enslaved on Atthow Pattison’s tobacco farm, situated across the river on the southeast side. Modesty gave birth to Harriet’s mother, Rit Green, there. When Pattison died in January 1797, he gave the enslaved girl “Rittia” to his granddaughter, Mary Pattison, with the stipulation that Rit and all of her future children be set free when “she and they arrive to forty-five years of age.”

Rit later moved to Madison when her owner, and young widow, Mary Pattison Brodess, married Anthony Thompson in 1803. There, Rit met and married Ben Ross and they started their own family. Atthow Pattison’s wish that Rit and her children eventually be set free was never honored.

Years later, Ben and Rit’s child Minty, the young Harriet Tubman, was hired to work for the James Cook family who lived near this bridge. Initially, Minty was expected to learn the trade of weaving. Instead, she was sent into the nearby marshes to watch Cook’s muskrat traps. It was harsh, dangerous work for a child, done in the winter, when muskrat furs are at their finest.

17. Brodess Farm

Where Harriet Tubman Was Enslaved as a Child
(Privately Owned)

Edward Brodess, Harriet Tubman’s enslaver, lived at this site. He moved Tubman’s mother Rit and her children to his farm in Bucktown after 1823 or 1824. Tubman spent her early years here and on nearby farms. No trace remains of Brodess’ original home that once sat near the existing house at the end of the lane.

Edward Brodess, with a small farm and few livestock, did not have enough work to fully employ all of his slaves. However, he had eight children to support, so he frequently hired his enslaved people out to neighboring farmers. Rit and her children suffered both emotionally and physically from these separations, one of the many injustices of the institution of slavery.

Harriet Tubman later told an interviewer that she seldom lived with the Brodesses. He was “never unnecessarily cruel; but as was common among slaveholders, he often hired out his slaves to others, some of whom proved to be tyrannical and brutal to the utmost limit of their power.” Harriet’s brothers, Ben and Robert, recalled harsher treatment at the hands of the Brodesses. Robert felt Edward Brodess “was not fit to own a dog.” Ben was more to the point: “Where I came from,” he later recalled, “it would make your flesh creep, and your hair stand on end, to know what they do to the slaves.”

18. Bucktown General Store

Site of Harriet Tubman’s First Act of Defiance

In 1835, Bucktown was a busy community with two stores, a shopkeeper’s home, blacksmith shop, and surrounding farms at this crossroads. Shipyards were nearby on the Transquaking River.

Hired out to a nearby farmer, Harriet Tubman and the farm’s cook went to a store at this crossroads to purchase some goods for the house. At the same time, a slave belonging to another master left his work without permission. His overseer pursued him to the store and ordered Tubman to help him tie up the man, but she resisted. Suddenly, the slave broke free and ran. The overseer grabbed a two-pound weight off the counter and hurled it toward him. It struck young Tubman in the head, almost killing her and causing a severe injury that troubled her for the rest of her life.

Tubman recalled “My hair had never been combed and it stood out like a bushel basket . . . I expect that thar hair saved my life.” The blow from the iron weight cracked her skull. “They carried me to the house all bleeding an’ fainting. I had no bed, no place to lie down on at all, and they lay me on the seat of the loom, and I stayed there all that day and next,” she later recalled. She was forced “to work again and there I worked with the blood and sweat rolling down my face till I couldn’t see.”

Operated by the Bucktown Village Foundation, 410-901-9255. Exterior can be visited dawn to dusk; interior open by appointment only. There may be a small fee for the interior tours.

19. Bestpitch Ferry Bridge

Marshland Secrets to Escape

Bestpitch Ferry Bridge is located at the site of a former ferry over the Transquaking River. This historic wooden bridge provides a view of Dorchester County marshlands. In this countryside, knowledgeable local people could hide for days, even weeks, and follow the waterways north toward Underground Railroad connections in the East New Market area, Caroline County, and onto freedom.

Many free and enslaved African American watermen operated ferry crossings throughout the region. They transported agricultural and timber products along the region’s many rivers on rafts. This provided opportunities for freedom seekers to hitch a ride or stow away in the holds and sail away to freedom.

The Blackwater and Transquaking rivers and their estuaries provided opportunities for local residents to hunt, fish and gather food for survival. Abundant fish and fowl live and breed in these waters, and many small and larger animals, including muskrats, rabbits, squirrels and deer live in nearby marshes and woods. Nuts, berries and a variety of roots and herbs round out the possible food and medicinal supplements available to 19th-century residents.

20. Scott’s Chapel

Drive-by Access Only

Harriet Tubman’s master, Edward Brodess, was a member of the congregation founded here in 1812. Tubman, her mother, and siblings may have worshipped here with other enslaved families and their owners.

Traditionally, the enslaved were required by their masters to attend church services with them, sitting in the back of the church or in balconies, separate from white congregants. The current building was constructed in 1891. The church has separate graveyards with blacks buried just east of Bucktown Road and whites buried behind the church and grove of trees. Members of the Bucktown community from Harriet Tubman’s time are laid to rest in this cemetery.

This is an active community church. Please respect the sanctity of the grounds and services.

Photo above credit of Chesapeake Bay Program

21. Pritchett Meredith Farm

Betrayed by a Black Underground Railroad Conductor

Drive-by Access Only

The flight of the “Dover Eight” made national headlines on March 8, 1857 when eight slaves escaped together from the Bucktown area, two of them from this farm. The group first sought help from Reverend Samuel Green in East New Market. Then they found assistance from Harriet Tubman’s father, Ben Ross, at Poplar Neck in Caroline County. Eventually they found their way to Thomas Otwell, a black Underground Railroad conductor in Delaware. Tubman trusted Otwell with the group’s safety. Instead, He betrayed her trust and lured them to the Dover jail so he could collect the $3,000 reward for their capture. With quick thinking and a show of force, the group successfully broke out of the jail and fled to Wilmington, then Philadelphia, and finally to Canada.

Local slaveholders sought swift and stern justice for anyone who assisted the “Dover Eight.” The Reverend Samuel Green was arrested and jailed on suspicion of aiding the group’s escape. Ben Ross nearly experienced the same fate, but Tubman rescued him just in time. Two of the eight escapees temporarily joined John Brown’s small army in Canada before the raid on Harper’s Ferry.

22. Faith Community United Methodist Church

Faith United Methodist Church and Rev. Sam Green

Sarah Young, a free black woman, deeded land to establish the Colored People’s Methodist Episcopal Church in 1844. Now known as Faith Community United Methodist Church, this church is the second structure to house this still-active congregation.

Reverend Samuel Green, a free black preacher, was one of the church’s first trustees. A highly respected preacher, he offered hope and resistance to slavery. His preaching did not escape the close scrutiny by white overseers, however. African-Americans regarded southern white ministers as part of the system of slavery. These ministers stressed obedience and patience.

Born in slavery, Green purchased his freedom in 1834. Within 10 years, he purchased the freedom of his wife, “Kitty.” His children, however, remained enslaved and out of his reach. In 1854, his son, Sam, Jr., fled to Canada, but Green’s daughter, Sarah, was sold away from her two little children and never seen again.

Green turned anger into action. As an Underground Railroad agent, Reverend Green helped Harriet Tubman and many others to freedom, including a group of freedom seekers called the “Dover Eight” in March 1857. He was caught and brought to trial. Unable to convict Green, the white jury acquitted him. He was soon charged with possession of Harriet Beecher Stowe’s novel, Uncle Tom’s Cabin, a violation of Maryland’s law governing possession of abolitionist literature by people of color. He was sentenced to ten years in prison.

23. Jacob and Hannah Leverton Home

Station House of Quaker Underground Railroad Agents
Privately Owned

Refugees from slavery found sanctuary here. One morning in the mid-1840s, a young enslaved woman, covered in bloodstained clothing, walked up to the Leverton farm. Jacob and Hannah took her in, nursed and fed her, and gave her clean clothing. Jacob was seen later that night traveling northward in his carriage with an unidentified guest. The young woman’s enslaver inquired about her at the Leverton home the next day. Jacob told the man that he had helped the girl and then “let her pass on.” The infuriated slave owner sued Jacob Leverton. Ordered to pay a large fine, Jacob became ill and soon died. His wife, Hannah most likely continued their Underground Railroad efforts. Jacob and Hannah Leverton were white, Quaker abolitionists. Their house has been described as “the main stopping place for the Underground Railroad in the region.” Along with the Levertons, free black millwright Daniel Hubbard and Quakers Jonah and Esther Kelley provided havens on their properties to help slaves reach freedom.

For more information, call 410-673-1910.

24. Linchester Mill

Enslaved and Free Blacks Working Side by Side

Daily life around Linchester Mill provided fertile yet dangerous ground for those seeking freedom. Whites and blacks, free and enslaved, would have regular contact here, at the general store or the post office. Free and enslaved African Americans worked side-by-side, providing a constant flow of information and support to freedom seekers. Quakers and free blacks who lived near the mill secretly helped fleeing slaves pass through the area.

A series of water-powered grist and sawmills operated here from the 1680s until 1979. The mill was situated amidst a secret network of safe houses: the Levertons, the Hubbards and the Kelleys on the west side, and Harriet Tubman’s parents Ben and Rit Ross at Poplar Neck on the east side. Daniel Hubbard, a known Underground Railroad conductor who lived less than a mile away, probably worked at the mill and may have helped build it. The milldam provided a possible crossing point over Hunting Creek for fugitives headed to the Ross home at Poplar Neck, to Marsh Creek Church or Preston and beyond. Such crossing points helped freedom seekers stay dry, particularly important in cold weather, and to avoid unwanted attention.

The mill is scheduled to be open April through October 2022 on the fourth Saturday of the month, 11am-4pm for docent led tours and Market Days.

25. Choptank Landing

Site of Harriet Tubman’s Most Daring Rescues

Harriet Tubman’s parents were active in the Underground Railroad in this area, and she most likely made her first escape from near here. Dr. Anthony C. Thompson employed Tubman’s father, Ben Ross on his 2,200 acres of heavily forested land in Poplar Neck during the late 1840s and 1850s. He also employed large numbers of free and enslaved black laborers in his timbering operations and sawmill.

On Christmas Day 1854, Tubman led her three brothers to freedom from Poplar Neck. Robert, Ben and Henry, and several others hid in a corncrib until dark, when they could begin their journey north. At nightfall, Tubman safely led them towards freedom, traveling through Delaware, Pennsylvania and across upstate New York to St. Catharines, Ontario, Canada.

Josiah Bailey, a skilled shipwright, escaped slavery in November 1856 by rowing a boat at night six miles from Jamaica Point in Talbot County up the Choptank River. He passed by here on his way to Poplar Neck. Then he met with Ben Ross, Tubman’s father, to plan his escape the next time Tubman was ready to go.

In March 1857, Ben Ross was suspected of aiding the escape of eight slaves, called the Dover Eight. Harriet Tubman rushed to the Eastern Shore to rescue her parents at great risk to herself before her father could be arrested. Cobbling together a makeshift, one-axle wagon, she rigged up a horse with a straw collar and drove her parents toward Delaware. They eventually made their way to St. Catharines, Ontario, Canada with the help of numerous Underground Railroad agents along the way.

26. Mount Pleasant Cemetery

Secret Meeting Place

This is the site of the original Mount Pleasant Methodist Episcopal Church, an African-American church community established in 1849 when local Quakers sold this land to free blacks, so they could build their own church. The congregation later moved to the town of Preston, where they still meet for services. This cemetery is still used by the church.

The cemetery may have served as a meeting place for fugitives on the Underground Railroad. Harriet Tubman was known to have used a cemetery as a rendezvous point for some of her escapes north. Laws restricted blacks from meeting in groups, and Tubman preferred to meet those who were fleeing with her in secret places away from their homes. She “was never seen on the plantation herself.”

Choosing a meeting place, sometimes miles distant, protected Harriet from discovery should any of the fleeing slaves get caught by their masters. A group of slaves gathering in a cemetery might not arouse the same attention as a group of black people gathering in a home, or even secretly in the woods, which was specifically forbidden by law.

27. Jonestown

Jenkins Jones established Jonestown as a community of free African-Americans in antebellum years. Jenkins and other free blacks wished to improve their destiny through education, so they founded a school and hired teachers to stay in the community and teach their children. The courageous Jonestown residents had the common bond of faith in God, which gave them hope for their future. They used this faith to empower themselves to create positive change for themselves. The people of Jonestown may have had connections in assisting Harriet Tubman and her rescue missions. Today, descendants of the original founders of Jonestown are successful professionals with firm roots in this community.

28. Webb Cabin

Typical African-American Home

James H. Webb, a free African-American farmer, built this hand-hewn log home around 1852 and lived here with his enslaved wife and their four children – Charles, Elizabeth, John and Ann, and Webb’s father, Henry. The family were members of nearby Mount Pleasant Church. The one-room home, with its “potato hole,” open fireplace, and loft accessed by a crude ladder, was built of materials found nearby. It sits on its original ballast-stone foundation from ships that plied the Chesapeake Bay.

Typical of housing for most African Americans at the time, this cabin is a rare survivor today. It also represents the kind of housing that sheltered many poor white families during the early and mid-19th century. Harriet Tubman’s father and mother, Ben and Rit Ross, probably lived in a very similar structure at nearby Poplar Neck.

The lack of resources and primitive characteristics of such buildings have long precluded preservation of many structures like this one. Webb’s cabin has been preserved for generations and utilized for a variety of purposes. The structure is owned and maintained by the Caroline Historical Society and sits on a one-acre plot of land owned by Caroline County.

29. Gilpin Point

Sailing Away to Freedom

Forty-year-old Joseph Cornish was enslaved by Captain Samuel LeCompte, married to a free black woman, and the father of five children. On December 8, 1855, Cornish most likely knew about the secret network Harriet Tubman relied upon in Philadelphia and New York, when he started out on “foot for Gilpins Point.” He had heard there was a vessel about to sail. He “worked his passage” to Baltimore, and then he made his way to Underground Railroad agent William Still in Philadelphia on Christmas Day. From there, Cornish was forwarded to agent Sydney H. Gay in New York City. He eventually made his way to St. Catharines, Ontario, Canada, where Harriet Tubman, her brothers and many others from Maryland’s Eastern Shore were settling into their freedom.

In the mid-19th century, Gilpin Point was one of the busiest wharves along the Choptank River. It served as a landing for passenger ships and merchant vessels. It sat just upriver from Dr. Anthony C. Thompson’s plantation where Harriet Tubman’s parents lived and where Harriet herself conducted several of her most famous escapes.

30. William Still Interpretive Center

Tragedy and Triumph on the Road to Freedom

William Still’s mother Sidney and four of her children lived in a house similar to this on Alexander “Saunders” Griffith’s plantation. Her husband, Levin Still, had been set free in 1798 by his young enslaver and resettled in New Jersey, hoping to bring his family there. Around 1806, Sidney escaped with her four children, but was soon recaptured.

After being locked away for three months, she was released and promptly fled again. In a heartbreaking decision, she was forced to leave behind two sons, Peter and Levin. Enraged by her actions, Griffith sold the two boys to slave traders from Kentucky. After joining her husband in New Jersey, Sidney renamed herself Charity, and the Stills raised a large family there. William, born in 1821, was the youngest of 18 siblings.

William Still became educated and moved to Philadelphia where he became Chairman of the Philadelphia Vigilance Committee of the Pennsylvania Anti-Slavery Society, assisting in the escapes of an estimated 1,500 freedom seekers. Harriet Tubman frequently passed through Still’s office, seeking protection and support for her rescues.

In 1850, Still realized that one of the men he was assisting was his own lost brother Peter, who had been sent to Alabama by his Kentucky enslavers years earlier. Peter’s later memoir, The Kidnapped and the Ransomed, raised enough funds to purchase his enslaved family. William Still’s documentation of more than 1,000 freedom seekers was published in 1871 as The Underground Railroad, one of the most important and authentic records of the operations of the Underground Railroad in history.

The Interpretive Center celebrates the Still family’s own daring and heart-wrenching struggle for freedom from bondage through escape, resettlement, and later, Underground Railroad activity. The center, housed in a historic one room “cottage” from 1820, features a period “slave cabin” interior, exhibits and a “garden patch” highlighting foodstuffs common in gardens cultivated by Eastern Shore enslaved people.

The house underwent restoration for years, and opened to the public in May 2022. Onsite signage tells the stories of the site from the time of Algonquin Indians, early commercial agriculture, and the William Still family connection. A glass rear door allows visitors to see inside the restored historic dwelling. The building does not offer any visiting hours, but visitors are welcome sunrise to sunset to view the building and peek through the glass door to see inside.

31. Caroline Courthouse

Site of Slave Auction and Jail

Although reconstructed after the Civil War, the courthouse’s place in the middle of town is symbolic of the central role it played in the past. The courthouse symbolized white legal, political, economic and social power during the antebellum period. A slave market was located here, where slaves were auctioned to buyers and traders. Courthouse Square was also the site of the jail where captured runaways and Underground Railroad conductors, like Hugh Hazlett, were held. Hazlett, a 27-year-old Irishman, was arrested in Greensboro for assisting seven people to escape slavery in 1858. After being jailed, Hazlett and the seven others were transported to Cambridge by steamboat for trial. Greeted by an angry mob, Hazlett was sentenced to 44 years in prison.

In 1853, African American residents celebrated the escape and return of Richard Potter, a free black youth, who had been kidnapped by a local farmer and smuggled to a Delaware boat captain to be sold as a slave. Punishments for “stealing slaves” or “enticing slaves away” or outright kidnapping included long prison terms, heavy fines, and confiscation of property.

For more information, call 410-479-2055.

32. Moses Viney Daniel Crouse Memorial Park

Challenging Slavery

Moses Viney was born into slavery in Talbot County, but escaped on Easter morning in 1840, after learning he might be sold to slave traders in the Deep South.

As a child, Moses played with his master’s son – Richard Murphy – who shared Moses’ birthday. When they turned seven, they weren’t allowed to play together anymore. Mr. Murphy sent Moses out to work in the fields. When Mr. Murphy passed away, Richard decided to sell Moses to the highest bidder.

Two men fled with him: Hinson Piney and Washington Brooks. Their flight from Talbot County brought them to Caroline County near Denton on the Choptank River. The slavecatchers’ hounds were fast on their scent, tracking them down. But Moses had prepared for this moment. He had been kind to those dogs for months – fed them, patted them. When the dogs approached Moses, he told them to go on home. The dogs wagged their tails, and bounded away. Moses found a canoe nearby without paddles. He took two fence posts and used them to row across the Choptank River near here.

The men traveled by night, hid out by day. They took a steamboat from Smyrna, Delaware to Philadelphia, then eventually reached Schenectady, New York. Moses worked as the personal carriage-driver to the president of Union College, Eliphalet Nott.

Ten years later in 1850, Congress passed the Fugitive Slave Law, allowing any slave owner to reclaim his “property” at any time, in any state. While Moses was driving President Nott’s carriage through town, there on the corner was Richard Murphy – his childhood friend and former enslaver – looking to reclaim his property. Moses rushed to Nott and begged for help. Nott helped Moses escape to Canada and paid Murphy $250 to leave Moses alone. Eventually, Moses came back from Canada, having escaped slavery for the second time.

33. Denton Steamboat Wharf

Once Thriving Port

During the 1850s, steamboats loaded with freight and passengers made weekly departures from Denton to Baltimore. Enslaved African-Americans worked in shipyards here on the Choptank River. When Underground Railroad conductor Hugh Hazlett was arrested for assisting enslaved people to flee, he boarded a steamboat here in 1858 on his way to trial in Cambridge, downriver, where he faced possible mob violence.

The Choptank River played a role in the history of slavery as much as any plantation field. At this point it was still wide and deep enough to serve as a barrier to escape for freedom seekers. Imagine the challenges they faced in trying to ford or cross waterways or hide away on vessels. Denton boasted not only an active port, but also a ferry crossing, and the Eastern Shore’s first moveable bridge structure spanned the Choptank here in 1811.

The Denton Steamboat Wharf also houses the Caroline County Office of Tourism.

For more information, visit www.tourcaroline.com or call 410-479-0655.

34. Tuckahoe Neck Meeting House

Quakers as Underground Railroad Agents
Privately Owned

Built in 1803, this was one of five Quaker meeting houses in Caroline County whose members sustained a local Underground Railroad network. Quakers also supported women’s equality and the end of slavery. By 1790, Quaker meetings on Maryland’s Eastern Shore were free of all slave owners. Quakers then became some of the earliest and most effective activists to end slavery in America and abroad.

They quickly began establishing a loose network of individuals with shared values who could be tapped to help escaping slaves find their way north, and provide support and shelter once they arrived. Abolitionist Hannah Leverton from the Linchester Mill area spoke here and was married here.

Quakers were at the forefront of the fledgling Women’s Rights Movement in the mid-19th century. Quaker women like Lucretia Mott, her sister, Martha Coffin Wright, and many others participated in the first women’s rights convention held in Seneca Falls, New York. Other powerful abolitionists and like-minded men and women supported them. Harriet Tubman would become close to many of these women, and through them, she would become involved with the women’s suffrage campaigns of the 19th and early 20th centuries.

35. Adkins Arboretum

Typical Woodland and Marshland

Adkins Arboretum is a 440-acre garden and preserve dedicated to promoting the appreciation and conservation of the region’s native plants. Walking along streams, over wetlands, and through woodlands allows visitors to experience the kinds of landscapes that freedom seekers on the Underground Railroad passed through on their way north.

The Arboretum offers programs year-round in ecology, horticulture and natural history for all ages, including special programming related to survival strategies used by fleeing slaves traversing these landscapes generations ago. Five miles of paths feature streams, meadows and rich bottomland forest.

Visit their website at www.adkinsarboretum.org.

36. Greensboro

Dangerous Crossing

In 1797, Greensboro resident Peter Harrington was president of the Choptank Abolition Society, formed to promote the end of slavery in Maryland.

Supported by Quakers, some Methodists, and others, regional societies like this worked on the local level. Petitions to the Maryland House of Delegates first focused on the trafficking of slaves and demanded an end to the exportation of slaves and free people of color.

Marketable goods were brought here, transferred to wagons and hauled to Delaware markets. Produce and timber products were delivered and shipped to ports near and far. Through these trade activities, Greensboro residents, free and enslaved, learned about religious revivalism, abolition and other new ideas. The northernmost bridge over the Choptank River was located in Greensboro. Though freedom seekers traveling north were tempted to use bridges, they usually avoided them, as the threat of recapture was high at these obvious crossing points.

In 1849, the year Harriet Tubman escaped, scores of freedom seekers fled nearby Talbot County. The slaveholders knew many were moving through Caroline County on their way to Delaware and beyond. Some of them, no doubt, passed near here. In August 1852, two men from Sandtown, Delaware, tried to entice a slave named Tom to escape. Tom informed his master, and an ambush was set to capture the two men in Greensboro. News reports suggested that the men were going to kidnap Tom and sell him to slave traders in the Deep South.

37. Red Bridges

A Place to Wade Across the Choptank

This stream at the headwaters of the Choptank River was possibly near Harriet Tubman’s Underground Railroad route to Sandtown, Delaware. The current at this location is fast, yet the water is shallow.

Freedom seekers who followed the Choptank River to Delaware may have crossed here and at other shallow tributaries near the Choptank’s headwaters. Like Harriet Tubman, fugitives relied heavily on the secret network of safe houses belonging to blacks and whites throughout central and northern Delaware. Harriet Tubman later told historian Wilbur Siebert that her preferred route was by way of her parents’ home in Poplar Neck, to Sandtown across the Maryland border.

While fugitives made parts of their journeys unaided, the assistance provided by a secret network of sympathetic people and those who ran safe houses was invaluable to their success. Throughout Delaware, communities of Quakers and a large free black population helped hide and escort runaways northward on their way to Pennsylvania.

38. Willow Grove

Crossroads to Freedom

Freedom seekers reaching the Delaware state line, also the Mason-Dixon Line, still were in a slave-holding state and had 75 miles to go before they reached the free state of Pennsylvania.

Harriet Tubman mentioned the crossroads of “Will’ Grove” to historian, Wilbur Siebert, in an 1897 interview about her Undergound Railroad journeys. She also noted other Delaware place names and key people. This byway route visits many of those sites. Willow Grove Road enters the state at Sandtown and travels through Willow Grove, where Quaker abolitionist Henry Cowgill and his family, and free black Underground Railroad conductor Samuel D. Burris lived. Across Willow Grove Road, abolitionist Henry Cowgill housed freedom seekers at his farm, according to oral tradition. The Historic Marker about Samuel D. Burris stands at the entrance to the Caulk Tract of the Norman G. Wilder Wildlife Management Area on Route 10/Willow Grove Road. Learn more about Samuel Burris’ story at the Old State House in  Dover and at the New Castle Court House Museum.

From this locale, fugitives could have chosen to venture to Camden, where free blacks Abraham Gibbs, and brothers Nathaniel and William Brinkley, joined forces to carry them further north. The travelers’ movements varied, but likely included pathways near and through Dover, Smyrna, Blackbird, Odessa, New Castle and Wilmington.

The Mason-Dixon Line was surveyed by Charles Mason and Jeremiah Dixon by 1767 to resolve a colonial border dispute. It was not made to separate states where slavery was illegal from those where it was legal.

39. Old State House

Taking Risks for Freedom

Start your visit at the First State Heritage Park Welcome Center (Delaware Public Archives) where you will find parking, amenities, and information on Park programming. The Center includes exhibits on Delaware history and founding documents. From there, it is a short walk to the Green, the Old State House and the John Bell House.

In 1847, Samuel D. Burris, a free black Underground Railroad conductor, was arrested, tried, and convicted in the courtroom of the Old State House for aiding the escape of slaves. In addition to large fines and jail time, a free African American convicted of such a crime risked sale into slavery. Spared that fate, Burris moved his family to California in the 1850s, where he continued to support the fight for African-American freedom. On November 2, 2015, Delaware Governor Jack Markell pardoned Burris in the same court room where he was convicted 168 years earlier. Tours and programs at The Old State House explore Delaware’s legislative debates on slavery and freedom.

The park also highlights the dramatic escape story of the “Dover Eight,” a group of freedom seekers and friends of Harriet Tubman, who fled from Maryland in 1857. They were betrayed by a black Underground Railroad agent, Thomas Otwell, who lured them into the Dover jail for a $3,000 cash reward. The group broke out of the jail in a dramatic altercation with the sheriff.

40. Blackbird

Landscape for Freedom Seekers

Harriet Tubman noted that a place called “Blackbird” was one of her landmarks as she journeyed through Delaware, but her precise pathways and stops here are not known. She may have been referring to one or more of the free black communities that once existed within the Blackbird Forest area. To the north are the historic towns of Middletown and Odessa, also important stops along the Underground Railroad. The 6,000-acre Blackbird State Forest evokes some of the landscapes that fugitive slaves and their guides would have encountered in parts of Delaware. These rich natural resources both hindered and enabled freedom seekers on their perilous journeys to the north. Blackbird State Forest offers 40 miles of trails and is popular with outdoor enthusiasts. Here you will find primitive campsites, picnic sites, seasonal hunting and catch-and-release fishing.

A short distance to the north is Middletown, a crossroads town between Odessa and Bohemia Landing, Maryland. Visitors will find a vibrant downtown of 19th-century historic buildings and shops, as well as suburban amenities. Toward the eastern end of town, the property of Middletown High School hosts a memorial park to the lives of freedom seekers and abolitionists.

A marker tells the story of Quaker abolitionists and Underground Railroad agents, John Hunn and John Alston, who once farmed the land there. It also commemorates the bravery of operative Samuel D. Burris and the freedom-seeking Hawkins Family.