The Enduring Legacy of Oak Bluffs, Martha's Vineyard

“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 Black history, 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.

This summer, Ralph Lauren is casting a renewed spotlight on the coastal destination with the launch of a limited-edition collection and campaign telling the story of Oak Bluffs. “This collection is about more than a charming coastal town; it’s a story of the American dream,” according to Ralph Lauren, executive chairman and chief creative officer of Ralph Lauren Corporation. “Oak Bluffs’ unique history, traditions and sense of community deeply inspire me and speak to what we are all searching for—a place where you can be free, uncontrived, joyful and truly at home.” The Polo Ralph Lauren for Oak Bluffs collection captures the East Coast energy of the island, with an offering that spans its iconic baseball hats, classic striped knits, and vacation-ready sundresses that speak to wardrobes of its longtime residents and vacationers alike.

Woldegebriel agrees: "There’s been a renewed energy in recent years." Citing more attention from national media, more investment in preserving its legacy, and more storytelling around its history, he insists that the charm of the island remains but that there’s a growing awareness of its cultural significance that's putting Oak Bluffs, and Martha's Vineyard at large, and on a larger platform. As for what's driving it, Woldegebriel says it all comes down to an increase in conversations around diversity and heritage. "Oak Bluffs offers an authentic narrative that can’t be manufactured: a living, breathing community with generational ties to Black excellence, style, and leisure."

As for where to head once you've reached its shores, Woldegebriel shares that his favorite spots include The Dragonfly House, a spot where he's hosted the annual Summer Bazaar for his label. Wandering Circuit Avenue for its mix of old-school charm and local businesses and grabbing a seat on the Inkwell Beach seawall at sunrise or sunset are also musts on his itinerary.

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