Frederick Douglass Museum and Cultural Center

The Douglass Summer House in Highland Beach is associated with the famed former slave and activist, Frederick Douglass, and his son, Major Charles Douglass, a Civil War veteran. With his father’s financial backing, Charles established the resort town of Highland Beach on the western shore of the Chesapeake Bay in 1893. Tradition has it that the younger Douglass was motivated to establish this African American vacation enclave five miles south of Annapolis after he and his wife were turned away from the adjacent all-white resort community of Bay Ridge. In 1893 he purchased 44 acres, including 500 feet of Chesapeake Bay beachfront and laid out streets named Douglass, Bay, Wayman, and Langston (the latter two named for Reconstruction-era friends of the family). The first two cottages built in Highland Beach were for father and son. Charles’s house was demolished in the 1950s but the house built for Frederick in 1894–1895 remains in excellent condition on its bayfront lot.

Also known as Twin Oaks, the Douglass Summer House is a two-and-a-half-story Victorian dwelling with a wraparound porch and wood-shingled hipped roof. In form and detail the house is a simplified version of the popular Queen Anne Style. Some accounts maintain that Frederick designed the house himself, including a second-floor balcony with views toward his birthplace on the Eastern Shore. However, he died in 1895 at Cedar Hill, his home in Washington, D.C, before ever living at the Highland Beach summer house. The south section of the porch was enclosed at an early date to serve as a kitchen and breakfast room.

Approximately ten more cottages were built in Highland Beach by 1910, including a large nine-bedroom house for George T. Bowen, a wealthy Baltimore caterer who was also a former slave. Highland Beach became a popular destination for those in the close-knit ranks of educated Black professionals. Famous visitors included educator Booker T. Washington, singer and actor Paul Robeson, and poet Langston Hughes. Around thirty more cottages were built between 1910 and 1930, many by distinguished Black residents of Washington, D.C. Prominent property owners included Dr. Johnny Washington, a dentist and collector of Lincolniana; poet Paul Lawrence Dunbar; Dr. William Wells, a pathology professor at Howard University; and Robert Terrell, Washington, D.C.'s first African American municipal judge, with his wife Mary Church Terrell, the celebrated educator and civil libertarian.

After Charles Douglass's death in 1921, the remaining lots were passed to his sons Haley and Joseph, with Haley emerging as a long-serving community leader. In 1922 Highland Beach became the first incorporated African American town in Maryland, and only the second incorporated town—after Annapolis—in Anne Arundel County. The Douglass family remained fixtures in the community, which gradually became a year-round residential neighborhood. The summer house stayed in the Douglass family until 1986. It was meticulously restored in the late 1980s. The State of Maryland and Anne Arundel County acquired the property in 1995 and deeded it to the Town of Highland Beach. It is now a museum and cultural center.