Spend a summer morning in Oak Bluffs and you'll feel it right away: the friendly hellos on Circuit Avenue, the colorful gingerbread cottages, the families who greet each other like they've been doing it for decades. Often, they have.

For more than a century, Oak Bluffs has been one of the most meaningful summer communities in the United States for Black families. It's a place where generations have gathered, bought homes, raised children, and returned year after year. Here's a look at that history, the people and traditions that shaped it, and how you can experience it thoughtfully on your next visit.

A Place to Gather

Black history on Martha's Vineyard reaches back centuries. Black and Cape Verdean mariners were part of the Island's whaling story, and William A. Martin of Edgartown became the Island's first African American whaling captain.

In the early 1900s, Oak Bluffs began to take shape as a summer home for Black families. At a time when many inns and resorts across the country would not welcome Black guests, Charles and Henrietta Shearer opened Shearer Cottage in 1912, an inn where Black visitors could stay, relax, and enjoy the Island. More than a century later, it is still run by the Shearer family's descendants.

Over the decades, Black families bought homes on Island, and many of those homes have been passed down through generations. For these families, Oak Bluffs became more than a vacation spot. It became a second home, built on hard work, community, and the simple joy of summer by the sea.

The Inkwell and the Polar Bears

Just steps from downtown Oak Bluffs, the stretch of Town Beach known as the Inkwell holds a special place in the Island's history. In the era of segregation, when Black visitors were not welcome on many beaches, this became the beach where Black families gathered. The origins of the name are debated, and today many in the community embrace it with pride.

The Inkwell is also home to one of the Vineyard's most beloved traditions: the Polar Bears. Since the 1940s, this group has gathered every summer morning for a swim, exercise, and fellowship in the waters of Nantucket Sound. From the Fourth of July through Labor Day, members arrive around 7:30 a.m., often entering the water singing the spiritual "Wade in the Water." The Polar Bears marked their 80th summer in 2026, and returning members often describe the mornings as a family reunion.

Writers, Leaders, and the Families Behind the History

Over the years, Oak Bluffs has welcomed writers, artists, and leaders whose work helped shape American life:

  • Dorothy West, the Harlem Renaissance writer, made her home in the Highlands, and her novel The Wedding draws on the Oak Bluffs community she knew so well.

  • Adam Clayton Powell Jr., the congressman and civil rights leader, spent summers at his cottage in the Highlands.

  • Dr. Martin Luther King Jr. visited the Overton House, the summer home of union organizer Joe Overton, which served as a gathering place for civil rights leaders in the 1960s.

  • Madame C.J. Walker, Paul Robeson, and Ethel Waters are among the notable guests who stayed at Shearer Cottage.

But the heart of this history isn't celebrity. It belongs to the teachers, nurses, ministers, business owners, and working families who saved, built, and returned summer after summer, and to the community organizations that have supported education and service on the Island for generations. Their homes, traditions, and stories are what make Oak Bluffs so special.

Experiencing This History Today

There are wonderful ways to learn about and celebrate Black history and culture on the Vineyard:

Check out the site Black Owned MV for a full directory of businesses. 

Visiting Respectfully

As you explore, remember that this history is also a living community:

  • Many historic sites are private homes. Enjoy them from the street.

  • Treat traditions like the Polar Bears' morning swim as the community gatherings they are, and ask before photographing people.

  • Look beyond the Inkwell. The Island's Black history runs much deeper, and a guided tour is the best place to start.

Planning your visit to Oak Bluffs? Explore more things to do, places to stay, and upcoming events across Martha's Vineyard at mvy.com.

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