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Before the Civil War, many enslaved African Americans fled to freedom by way of a secret network of roads, waterways, trails, and hiding places that became known as the Underground Railroad.
They were helped along the way by black and white anti-slavery activists. 
Harriet Tubman was the most famous “conductor” on the Underground Railroad. Born a slave in Dorchester County about 1821, she fled to the North in 1849. Over the ensuing decade
before the Civil War, despite a bounty for her capture, Tubman returned to the South nearly 20 times and led as many as 300 slaves to freedom, including many of her immediate and extended family.
The Underground Railroad Scenic Byway, established by the Maryland State Highway Administration, highlights the life of Harriet Tubman and many historic places
connected with her. From Dorchester County and scenes of her early life, you can follow the trail north through Caroline County, where many Maryland free
blacks and white abolitionists supported the cause of freedom.
The Cambridge city and Dorchester County sites include: 
o Harriet Tubman Memorial Garden.
o Underground Railroad
Museum and Gift Shop, home of the Harriet Tubman Organization.
o Bethel AME Church, which Tubman may have attended.
o Dorchester County Courthouse, where the legal
debate over ownership of Tubman convinced her to attempt her escape.
o Harriet Tubman historical marker, near the site where Tubman lived as a child.
o Bucktown country store, probably where Tubman was struck in the head around 1835.
The Choptank River was an important path northward from Dorchester through Caroline County, where
Quakers and other abolitionists were well established. The Choptank was probably used many times by Tubman and her "passengers" on their northward journeys.
The table below highlights sites along the Underground Railroad Scenic Byway
that are connected to the Choptank River in Caroline County. It also lists public landings where you can enhance your Scenic Byway experience by "touching" the river at
various points along this water escape route to the North.
The complete Underground Railway Scenic Byway Guide is available for download (in PDF format). You can
also order a Scenic Byways road map online from Maryland SHA, and obtain the companion booklet by calling 1-877-MDBYWAY (1-877-632-9929).
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Distance:
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64 Miles by Road; paddling opportunities in the Choptank River at many points along the route.
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River:
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Lower & Upper Choptank
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Start:
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Cambridge
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Destination:
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Denton, then Delaware via Goldsboro
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Route Description:
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Follow the Underground Railroad Scenic Byway guide to historic sites in and near Cambridge; then follow the guide north along the Choptank River through Caroline County to Delaware.
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Themes:
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African-American History, Small Town Life
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Best Seasons:
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Year-Round
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Choptank River Sites
Associated with Underground Railroad History
For route details, see the Underground Railroad
Scenic Byway Guide.
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Point of Interest
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River
Mile
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Features
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Cambridge
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13
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Many sites connected to Harriet Tubman and the Underground Railroad are in and around Cambridge:
Harriet Tubman Memorial Garden, Bethel AME Church, Underground Railroad Museum and Gift Shop, Dr. Anthony Thompson farm, Bucktown Country Store, Harriet Tubman Birthplace Historical Marker.
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Caroline County, Hunting Creek farmlands, MD 16 at Preston Rd.
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24
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Area of farms of Daniel Hubbard, a free black farmer and fisherman, who was familiar with the Choptank as a water route, and Arthur Leverton, awhite Quaker farmer. Suspected of helping
runaway slaves caught on New Year’s Eve 1857; threatened with lynching and forced to leave Maryland.
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Preston, Hunting Creek
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24
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Site of Linchester, one of the oldest settlements in Caroline County, and gristmill established in 1681. Side trip to Mt. Pleasant Cemetery, site of old Quaker meeting house deeded 1849
to black Methodist trustees, possible stop on the Underground Railroad.
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Choptank (town)
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24
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Side trip from Preston to this river hamlet; excellent paddling on the wide lower Choptank or in adjacent Hunting Creek to Back Landing.
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Bureau
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38
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From Preston north on MD 16 north, pass through Jonestown, Harmony, and and Bureau, named for the Freedmen’s Bureau building built there after the Civil War.
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Two Johns Landing
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40
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On MD 16, look for the sign to the community of Two Johns.
An unmarked public landing gives paddlers access to the upper Choptank. Explore this section of the river where free black fishermen may have hidden passengers while continuing north through Denton and Greensboro.
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Denton
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44
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In the spring of 1857, Harriet Tubman learned that her father, a free black, was about to be arrested for helping fugitive slaves escape from Dorchester County.
She led her parents secretly to abolitionists in Wilmington, Delaware, who gave them money to go to Canada. Had they not fled Caroline County, her father would probably have stood trial in the Carline County courthouse.
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Choptank Mills on Mud Mill Pond, on the Upper Choptank River, Delaware state line
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66
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Extend your Byway experience by continuing north from Goldsboro on MD 313. Follow back roads and cross the Choptank River near its mashy headwaters. Not home free yet, fugitive
slaves may have crossed through these marshlands into Delaware, where President Lincoln hoped that an early emancipation plan would be adopted before his Proclamation.
Amish and Quakers in northern Delaware, and abolitionists in Wilmington, near the Mason-Dixon line, assisted the Underground Railroad.
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