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