The Eastern Shore of Maryland: An African-American History Tour

When most people think of the Eastern Shore of Maryland, they think of crabs, watermen, and the colorful history portrayed in Michener’s Chesapeake. Another important historic aspect of the Eastern Shore is its deep African American heritage and the Underground Railroad, the setting for hundreds of escaped slaves on their way to a life of freedom in the North.


One of the heroines of the Underground Railroad was Harriet Tubman, (1820-1913) known as the “Moses of her People,” who risked her life countless times returning to her native Eastern Shore to bring hundreds of slaves to freedom in the North. During the Civil War, she served the Union army as a nurse, scout and spy.  History buffs can learn all about this immensely brave woman and the Underground Railroad movement during a road trip around the Eastern Shore of Maryland.

7229_139292738810_77835348810_2698068_6692215_nA secret underground network of trails across land and waterways spanned across the Eastern Shore and the large Quaker population, along with other sympathetic whites, provided food and respite for these runaway slaves.

An officially designated Maryland Byway, named “Harriet Tubman’s Underground Railroad,” spans 64 miles, with markers mentioning Tubman, abolitionist Frederick Douglass, also from this area, as well as fellow Underground Railroad “conductor” Samuel Green and others. A map of the tour is available through the State of Maryland and at various Maryland visitor centers.

Easton is a central point where one can stay to visit various historic sites to its north, east and south; pivotal points in the Underground Railroad and the life of Harriet Tubman.  Staying in a historic inn will complete the experience.

The Bishop’s House in Easton is a Victorian clapboard and gabled home featuring period-style furnishings and working fireplaces. A sumptuous full breakfast is served every morning. It’s nestled in Easton’s Historic District, within three blocks of boutiques, antique shops, restaurants and the courthouse where the trial of preacher and “Railroad” agent Samuel Green was held.

Nearby historic sites include the birthplace of Frederick Douglass, who was born on Tuckahoe Creek and lived as a slave in the St. Michaels area. Douglass taught himself to read and write and conducted clandestine schools for blacks. After escaping north, he became a noted abolitionist orator and editor. He returned south in 1877, as U.S. Marshal for the District of Columbia, and served as D.C. Recorder of Deeds and U.S. Minister to Haiti.  The quaint but popular St. Michael’s, home to the Chesapeake Bay Maritime Museum and a host of upscale shops and restaurants, makes a nice overnight stop.   The lovely Aida’s Victoriana Inn offers a serene view of the Marina area and the Maritime Museum.

Unionville in Talbot County is a historic African-American community settled by ex-slaves and free blacks. Many served in the Union Army during the Civil War. Interned in its cemetery are 18 black Union soldiers. Unionville grew after the war to nearly 40 buildings with a church and school.

The locations of several daring group escapes led by Harriet Tubman are up the Choptank River in Preston, where her parents later lived before their escape to freedom, as well as at significant stops along the river in Denton.

Scott's Methodist ChurchHeading South to Cambridge and the Dorchester County Visitor Center overlooking the river, you can learn about the Underground Railroad, then visit the Harriet Tubman Museum and Education Center. Drive through picturesque countryside to nearby Bucktown and see the plantation where Tubman was born and toiled along with hundreds of slaves before her escape.  View the church where she worshipped, and some of the trails and rivers on which she returned and led many slaves to freedom.  Tour some of the Quaker homes and churches which gave sanctuary and assistance along the way.  Go inside the oldest one room school house for black children, the Stanley Institute, begun in 1867, which was still in use until 1962.  Nearby is the historically preserved Bucktown Village Store, the site of Tubman’s first act of defiance.

The inn Lodgecliffe on the Choptank, built in 1898, is poised on a bluff overlooking Choptank River in Cambridge and offers outstanding accommodations and a magnificent water view
To continue your African-American History Tour of the Eastern Shore, head southeast along route 50, through Trappe, the home of Nathaniel Hopkins, who served in the United States Colored Troops during the Civil War and returned here to assist newly freed blacks, establishing Talbot County’s first school for black children. Then continue east on Rt. 50 to Mardela Springs, then turn east  on Rt.54-Delmar Rd to see one of the few surviving historical markers of the Mason Dixon line, which separated the North from the South during the Civil War (on your left just before the Delaware state line). Continue back on 50 and head southeast to Rt. 13 and Princess Anne in Somerset County, the location of one of the oldest black colleges in the US.  The University of Maryland Eastern Shore (UMES) is a land-grant, historically black college founded in 1886 as the Delaware Conference Academy and features the impressive Frederick Douglass Library with its magnificent mural of Douglass and Tubman.  The picturesque historic campus is open for touring; don’t miss the Tuskeegee Airmen exhibit in Henson Hall. One can stay at the town’s unique Alexander House Booklovers B&B in the Langston Hughes Room, a “celebration of the Harlem Renaissance and black history.” Photos of contemporary black authors adorn the staircase of the inn.

In Princess Anne, the Teackle Mansion (open for tours), was owned by a wealthy ship owner who opposed slavery; it’s rumored to have been a riverside embarkation on the Underground Railroad, but this has not been confirmed. The mansion and a nearby row of former slave tenant houses are a few blocks walk from the bed and breakfast.

There are several historic black churches in and around Princess Anne, including the church attended by Anthony Johnson, the first free black man in America, a large land and slave owner himself in the late 1600s who owned 300 acres in Somerset County and several hundred in Virginia. Ironically, the legal precedent establishing slavery in Virginia in 1654 was based on the case of Anthony Johnson pleading his right to keep his black slave, John Casor, for life. (Anthony Johnson on Wikipedia)

The Manokin District of Somerset is the first Maryland district settled by freemen.
Click Here. For a map of African American historical sites in Somerset County.

15 miles further south, Pocomoke is the setting for The Sturgis School House and Museum, an African-American school built about 100 years ago and wonderfully restored with period furnishings and exhibits. (

From Pocomoke, one can head east along Rt. 113 to Berlin and the home of Charles Albert Tindley (1851-1933), one of the most famous African-American ministers of his era and “one of the founding fathers of African American Gospel music.” His songs, Stand By Me and We Shall Overcome are musical icons.

In Berlin, stay in a magnificent pre-Civil War mansion, the Merry Sherwood Plantation, located just off Route 113.  Likely built using slave labor, Merry Sherwood is a “50-foot tall explosion of Gothic, Greek Revival and classic Italianate architecture.”  Boasting 27 rooms and 8,500 square feet, the mansion was the largest house in Worcester County when constructed in 1859.

End your tour driving through Ocean City, location of the historic Henry Hotel on the corner of South Division Street and Baltimore Avenue.  Formerly known as “Henry’s Colored Hotel,” the wood-shingled structure built in the 1890s is one of the oldest hotels in the city and the last hotel that served black visitors to the ocean resort during the early to mid-20th century.   Duke Ellington, Cab Calloway, Count Basie and Louis Armstrong were all guests there.

Somerset County:
Talbot County:
Worcester County:
Dorchester County:
For more information on Harriet Tubman:
More on the Underground Railroad in Maryland: