In 1893, Charles Douglass, son of the famous Frederick Douglass, was denied entry into a white-only resort in Bay Ridge, Maryland. Upset, Douglass purchased his own plot of beach land from a nearby black farmer. Although the land was as small as two city blocks, it became it’s own getaway for blacks, and gave root to a new vacation spot that was free from racism. The area was known as Highland Beach.

Intellects like Paul Robeson, Booker T. Washington, W.E.B. Dubois, Langston Hughes and Paul Laurence Dunbar were found at the small, but quaint Highland Beach. Douglass built his father a home on the beach and named it Twin Oaks. It was meant to be his father’s place to reflect on his life as a former slave turned a free man with property and prosperity. Unfortunately, Frederick Douglass passed away before the home was complete. Since 1922, the beach had been run by its own ‘government,’ which was said to have attributed to its survival during the Jim Crow era.

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