What we did on our summer vacations: The history of Highland Beach

As we bear the peak of the summer heat, theGrio celebrates the legacy of Black summer retreats, including Highland Beach, Md., co-founded by Frederick Douglass' son Charles.

Highland Beach Maryland theGrio.com
"Highland Beach" by MDGovpics is licensed under CC BY 2.0.
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With the summer swiftly coming to a close, what, if anything, did you do during your summer vacation? If you’re anything like us here at theGrio, you not only enjoyed a little time off but also reflected on retreats made popular by Black vacationers of the past; one of which is the oldest known Black resort town in America, thanks in large part to an iconic heritage.

Highland Beach Maryland theGrio.com
Photo: Creative Commons; “Highland Beach” by MDGovpics is licensed under CC BY 2.0.

The town of Highland Beach, Maryland was founded in the late 19th century by Charles Douglass, son of famed abolitionist Frederick Douglass, and Charles’ wife, Laura. In the era of Reconstruction, the couple was among several newly affluent Blacks seeking retreats in the Chesapeake Bay. According to the Black Information Network, after a racialized rebuff at an area restaurant, Charles was inspired to try his hand at real estate, acquiring beachfront properties which he then either developed or resold to family, friends, and other prominent Black residents, attracting a community which would eventually include Booker T. Washington, Paul Robeson, Harriet Tubman, W. E. B. Du Bois, Langston Hughes, Paul Laurence Dunbar, and author Alex Haley, among others.

Incorporated in 1922 and remembered as a “utopia that left Jim Crow on the other side of the Chesapeake Bay Bridge,” as noted by local station NBC-WBAL, the 92-home enclave is still primarily Black-owned, led, and occupied, with most residences handed down via generational wealth. In fact, unlike other historic Black resort towns like Oak Bluffs in Martha’s Vineyard, Highland Park is largely inaccessible as a summer destination. As of 2018, only one home was available as a summer rental.

Highland Beach isn’t an anomaly; what both the locale and its legacy signify is a long-held tradition of safe spaces created exclusively for Black patrons to retreat to and enjoy. While there are undoubtedly classist implications to the availability of these destinations, there is an equally rich history borne out of the needs and accomplishments of a striving Black populace, often the first generation free from enslavement. And though the need for exclusively Black summer retreats may have somewhat outlived its usefulness, the legends of these enclaves live on.

Maiysha Kai is theGrio’s lifestyle editor, covering all things Black and beautiful. Her work is informed by two decades’ experience in fashion and entertainment, great books and aesthetics, and the brilliance of Black culture. She is also the editor-author of Body (Words of Change series).

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