Main Street, Hillsboro, Maryland 21641
Our Douglass tour intersects here with the Civil War Trail. You are now two-plus miles north of Frederick Douglass’s birthplace as the crow flies and about four miles north as the river winds. The c. 1790 Federal-style brick house behind you on the hill was there in Douglass’s childhood. The view directly across the river is a 40-acre tract donated by the Moore family which is now part of Frederick Douglass Park at Tuckahoe. Note the interpretive sign depicting both Douglass and his wife Anna Murray Douglass, who was born free near Denton, Maryland. Though they were neighbors in youth, Douglass’s three narratives relate that he met Anna in Baltimore. They were married in New York after his escape, which she helped to fund, in 1838, and settled in New Bedford, Massachusetts. Rev. J.W.C. Pennington, who was also born enslaved on the Eastern Shore in nearby Queen Anne’s County, performed the ceremony. By 1849, the couple had five children: Rosetta Douglass, Lewis Henry Douglass, Frederick Douglass, Jr., Charles Remond Douglass, and Annie Douglass.
Canoes and kayaks may be put in here for a river tour of Douglass’s childhood neighborhood. Navigate south to Covey’s Landing.
“Upon receiving this [marriage] certificate … I shouldered one part of our baggage, and Anna took up the other, and we set out forthwith to take passage on board of the steamboat John W. Richmond for Newport, on our way to New Bedford.”
—Narrative of the Life of Frederick Douglass, an American Slave