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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.

As desegregation opened up many other vacation spots to African-Americans, residents stopped frequenting the historic Highland Beach. By the 1970’s visitation had decreased, until the year 2010. Older generations that remembered the significance of Highland Beach returned to retire, breathing new life into the small plot of well-kept land. A guard now keeps the historical beach, which is open to the public and local residents.

Twin Oaks now serves as a historic landmark and museum. It is maintained by neighbors who also happen to be the descendants of civil rights activist and a founder of Delta Sigma Theta Sorority, Inc., Mary Church Terrell. The area continues to fill with families directly related to the prominent blacks that once inhabited Highland Beach and made it the vacation spot free from racism.