Highland Beach, Maryland, the oldest of the major black resort towns, was founded along the western shore of Chesapeake Bay in 1893 by Charles and Laura Douglass. Charles Douglass was the son of prominent abolitionist and 19th century civil rights activist Frederick Douglass. Major Charles Douglass, however, was prominent in his own right. He was a retired officer formerly with the 54th Massachusetts Colored Infantry, the famed regiment first established during the American Civil War, and longtime Treasury Department clerk.
Located in Anne Arundel County, 35 miles east of Washington, D.C. and a few miles south of Annapolis, Maryland, Highland Beach became the first African American-owned summer resort community in the United States. In fact it was established because of an act of racial discrimination. In 1890 Major Douglass and his wife were denied entry into a restaurant at The Bay Ridge Resort on Chesapeake Bay because they were African American. In response Douglass entered the real estate business and began purchasing beachfront property directly south of Bay Ridge. When he acquired slightly more than 40 acres for $5,000 he began developing the property as a summer resort community by selling 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. Robert Terrell was the first black judge in the District of Columbia.
Charles Douglass also began building a large family summer house which he named Twin Oaks. Intended primarily as a retirement residence for his father, Twin Oaks soon became a gathering place for many influential African Americans who lived in the Washington-Baltimore area but who visited Frederick Douglass there. Although Fredrick Douglass died before he could move permanently into the house, Highland Beach, as the surrounding community was now called, quickly became popular with prominent African Americans. Part-time residents and guests over the years included a who’s who of black America including Paul Robeson, Booker T. Washington, W.E.B. DuBois, Langston Hughes, Robert Weaver, and Alex Haley.
Charles Douglass claimed his greatest success in establishing Highland Beach was in circumventing restrictive property covenants in the area that prevented the sale of real estate to blacks and other people of color. Originally intended as a summer resort, Highland Beach by 1915 was a year round community with many houses and properties still retained by descendants of the original owners.
When founder Charles Douglass died in 1920, the town’s leadership fell into the hands of his son, Haley Douglass who in 1922 led the effort to make Highland Beach the first African American incorporated municipality in the state’s history. Once incorporated, Douglass and his allies controlled the community for the next three decades and succeeded in their major objective, insuring that the community remained small and exclusive.
Ironically in the community’s determined effort to keep newcomers out, it could not control the land surrounding Highland Beach. Beginning in the 1940s white and black developers built competing resort communities that attracted newly affluent African Americans. Also, the older formerly all-white resort community of Arundel-on-the-Bay had become predominately black by 1960.
By the 1990s the combination of high taxes, encroaching upscale housing developments filled with luxury homes, and the flight of younger blacks to newer resorts, left the elderly residents of Highland Beach increasingly isolated. Only about 1,000 residents remained in the community by 2010.