‘Summer House: Martha’s Vineyard’: How Did the Vineyard Become a Popular Black Vacation Spot?

Bravo’s new iteration of Summer House has all the reality TV ingredients of a wild party, but the newest destination of Martha’s Vineyard has an important history behind it. The Summer House: Martha’s Vineyard features a Black cast of attractive millennials who embrace the work hard/party hard mantra Summer House is known to embody.

But by peeling back the layers of this small Massachusetts island, there’s more to the destination than just tequila sodas and endless hookups. The island is comprised of several small towns, and specifically, Oak Bluffs has deep meaning and appreciation to the Black community.

Also known as “The Inkwell,” Oak Bluffs and Martha’s Vineyard is a favorite vacation destination for decades. The island also attracts hugely famous and powerful people, including President Barack Obama, director Spike Lee, Oprah Winfrey, and many others.

What is the history of Martha’s Vineyard for Black vacationers?

The island connection to the Black community began during slavery.  “Martha’s Vineyard was part of the underground railroad, so it was known as a safe and welcoming community for African Americans,” Nancy Gardella, executive director of Martha’s Vineyard Chamber of Commerce told Vox. “They didn’t feel entirely welcome in other beach enclaves.”

Former broadcaster Skip Finley told Vox that his family has vacationed on the Vineyard for years and shared why. “I don’t have to catch my breath here,” he explained. “It’s the freest place I’ve ever been.”

Finley believes that about 30% to 35% of the summertime island population are Black or people of color.  “I can be who I want, when I want. Which is not necessarily true of the rest of the country,” Finley added. “When we get on a boat or plane to leave here, we call it ‘going to America.’”

How did Oak Bluffs get the name ‘The Inkwell’?

The Town Beach in Oak Bluffs earned its moniker of “The Inkwell” when it became a popular beach spot for Black vacationers in the late nineteenth century. Oak Bluffs also become a popular town for vacation home purchases, specifically the quirky and adorable gingerbread cottages surrounding the campground in town.

“Women made up most of the first African American entrepreneurs and played a pivotal role in attracting and accommodating the growing number of black visitors to the Island,” according to Black Past. “Shearer Cottage, founded by Charles and Henrietta Shearer in 1912 as a summer inn, actually began as a laundry operated by Henrietta which opened in 1903.” 

“The Cottage is the oldest and most well-known of these establishments that catered specifically to African Americans. Their daughters, granddaughters, and great-granddaughters have continued management of the family’s guest house into the twenty-first century.”

Oak Bluff’s history as a Black vacationer spot was fictionalized in the 1994 film The Inkwell. The film, which starred Jada Pinkett Smith and Larenz Tate followed two families in the summer of 1976.

‘Summer House: Martha’s Vineyard’ teases ‘Black excellence’

While the Summer House: Martha’s Vineyard trailer teases the typical party atmosphere known for the series, hopefully, the show dives into the rich and important history of the island.

“For more than 100 years, Black vacationers have flocked to Martha’s Vineyard, an island south of Cape Cod, Massachusetts, and one of the first beach destinations where African Americans could vacation and purchase property,” according to Bravo.

“Known for its natural beauty with pristine beaches, romantic sailboats, colorful gingerbread cottages, and cultural identity, this summertime sanctuary has become a favorite escape for the rich, famous, and politically connected,” the release continued. “Summer House: Martha’s Vineyard follows a group of 12 friends as they enjoy their island getaway. With beach parties, decadent dinners, and summer hookups, both fun and drama are in store for these young Black professionals and entrepreneurs.”

Summer House: Martha’s Vineyard debuts on Sunday, May 7 at 9 pm ET on Bravo.