"The Vineyard is such a sacred place," shares Áwet Woldegebriel, the founder of his eponymous New York fashion label. Like the many creatives who call the island home, Woldegebriel has been returning each summer for nearly a decade, rarely spending more than a few months away. For many of its residents, that pull is similarly visceral. In his memoir, I Regret Almost Everything , celebrated restaurateur Keith McNally describes his first impression of Martha's Vineyard while awaiting the ferry from mainland Massachusetts. "Watching the Nantucket passengers saunter ashore," he writes in the book, "I was put off by how white and preppy they all looked and much preferred the look of passengers coming off the second boat: a mixed bag of farmers, dropouts, and long-haired academics… I quickly switched tickets."
Set just 28 miles across the Nantucket sound from its neighboring island, the Vineyard has remained the antithesis of the wealth, pedigree, and exclusivity that have come to define Nantucket—and its residents are keen on keeping it that way. The island's working-class roots aren't the only thing that sets it apart, though. Perhaps more than any other resort destination along the East Coast, Martha's Vineyard has a rich and layered legacy that's uniquely steeped in Black history.
"It's not just beautiful beaches and postcard views," says Woldegebriel. "It's a place steeped in creativity and resilience. That legacy, coupled with a deep sense of community, is what keeps me coming back. It's one of the few places where you can feel both completely at ease and deeply connected to a greater story." The island at large may be known for the picturesque white picket fences and vivid hydrangeas of Edgartown and the A-list enclave where the Obamas spent several summers over in Chilmark, but it's the town of Oak Bluffs on the northeast shore that, as Woldegebriel puts it, "has always been a heartbeat for Black joy, culture, and gathering."
Today, Oak Bluffs is a beloved retreat for family vacations and community gatherings, but its roots as a haven for Black travelers dates back to the Civil War era, when the island was a part of the Underground Railroad system. During the height of Jim Crow laws, Oak Bluffs institutions like the Dragonfly House, a former inn that now serves as a community center, were deemed safe havens for Black travelers in the Green Book . As such, many prominent figures have sought out its shores—from the poet Langston Hughes to Gabrielle Union and Dwyane Wade.
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