If you have never heard of Highland Beach, located just south and east of Annapolis, you should know that it is the first African American Municipality incorporated in Maryland, in 1922. 
The history of this small beach town, with street names honoring leading African Americans like Dunbar, Henson, Augusta, Douglass, Langston, and Washington, began in 1892. Maj. Charles Douglass, Civil War veteran and the first African American to enlist in the New York military, was refused service when he and his wife stopped for dinner at the Bay Ridge Resort Hotel during a summer outing near Annapolis.
Maj. Douglass relayed their experience to his father, activist and famed orator, Frederick Douglass, and the seeds of Highland Beach were sown. Through a chance encounter, Charles Douglass met Daniel Brashear, a Black Anne Arundel County farmer, waterman, and heir to 48 acres of waterfront property directly adjacent and to the south of the Bay Ridge Resort. 
With the aid of his father, Maj. Douglass negotiated a 2/3 interest in the property located only 35 miles from Washington. In 1893, he purchased almost 27 acres of the land and began developing it as a private summer resort community for Blacks. The Major sold lots to family and friends. Among the earliest purchasers were Blanche K. Bruce, the Reconstruction-era U.S. Senator from Mississippi, former Virginia Congressman John Mercer Langston, former Louisiana Governor P.B.S. Pinchback, Washington hotel owner James Wormley, and Judge Robert Terrell and his wife, Mary Church Terrell, a teacher and activist. Robert Terrell was the first black judge in the District of Columbia and Mary Terrell was one of the first Black women to earn Bachelor’s and Master’s degrees. Other notable residents were actor Paul Robeson, Booker T. Washington, writers Alex Haley, Paul Lawrence Dunbar, and WEB Dubois, Robert Weaver, the first African American cabinet appointment, and sociologist E. Franklin Frazier. In its heyday it was considered the Riviera of Chesapeake. 
Major Douglass built a home, Twin Oaks, for his father, Frederick Douglass, in Highland Beach. Frederick Douglass died before its completion. It was restored in 1987 and The Douglass Summer House was listed on the National Register of Historic Places in 1992. It now houses the Twin Oaks Frederick Douglass Museum and Cultural Center.
After the death of Charles Douglass, his son, Haley Douglass incorporated the town and served as mayor until his death in 1954. Many lifelong matches were made at the beach. Dr. Frederick Douglass III, great grandson of Frederick Douglass, married the granddaughter of Booker T Washington, joining two of the most esteemed Black families of the 19th and 20th centuries.
Most Highland Beach properties have passed from generation to generation. In 2018, a survey found that just over 53% of the town residents identified as Black, reflecting the principle of equality at the heart of Frederick and Charles Douglass’ experiment.