Highland Beach was founded in the summer of 1893 by Charles Douglass (Frederick Douglass' son) and his wife Laura after they had been turned away from a restaurant at the nearby Bay Ridge resort because of their race. They bought a 40-acre (160,000 m2) tract on the Chesapeake Bay with 500 feet (150 m) of beachfront and turned it into a summer enclave for their family and friends. It became a gathering place for upper-class blacks, including many of the well known personages of the age.
Among the residents and guests were Paul Robeson, D.C. municipal court judge Robert Terrell and his wife Dr. Mary Church Terrell, Robert Weaver, Harriet Tubman, W. E. B. Du Bois, and poets Langston Hughes and Paul Laurence Dunbar. Charles Douglass’ father, the famous abolitionist Frederick Douglass, visited and would have become a resident had he not died before the house that his son was building for him was completed.
When Highland Beach was incorporated in 1922 it became the first African-American municipality in Maryland. Although founded as a summer resort, it is now a town of year-round residents who choose not to permit commercial establishments. There are some sixty homes, many of them still owned and occupied by descendents of the original settlers. The residents are proud and protective of their town’s heritage, established over a century ago by proud and successful people determined to overcome the prejudices of their post-Reconstruction times. However, it should be noted that, as of the 2000 census, African-Americans make up less than 40 percent of the towns residents.