Beyond the beautiful beaches and glitzy galas, Oak Bluffs is a complex community that elite families, working-class locals and social-climbing summerers all claim as their own.
Archival photos courtesy of the Collection of the Smithsonian National Museum of African American History and Culture, Gift of Dr. Teletia R. Taylor and descendants of Geraldine A. Taylor, Proprietor: “Taylor’s Playfair.” All other photos by Christine Sargologos.
Elizabeth Gates was 12 the first time she snuck out of her family’s summer house. From the balcony of their white antebellum home, Gates could hear Biggie rap lyrics pulsing through her window, and she quietly made her way down to the beach where a mass of people were dancing in the thick, steamy air. That was how so many summers played out until Gates turned 16, when she no longer had a curfew and could finally stay out all night reveling in the beach parties and bonfires that drew heavy crowds to Oak Bluffs, a quaint town on the northeastern shore of Martha’s Vineyard, a 96-square-mile island shaped like a shark’s tooth off the coast of Massachusetts.
“It was this hub of relaxation, and a marker for all my rites of passage,” says Gates, a writer and the daughter of public intellectual and African-American scholar Henry Louis Gates Jr. In the past, Oak Bluffs has been hailed as a summer playground for the elite, but that neat summary doesn’t tell the full story, as interviews with close to a dozen summertime vacationers and longtime residents recently showed. As in any place with a treasured history, powerful personalities, breathtaking vistas and scarce acreage, there is tension: between longtime residents and newcomers, between year-rounders and those who summer, between old and new. And always, there is the fear that as this cherished community continues to evolve, it will lose the very things that make it so special.
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Oak Bluffs became a tourist destination out of necessity. Named for its scenic perch in an oak grove overlooking the Nantucket Sound, in the Atlantic Ocean, it was a haven for African-Americans during the mid-20th century when Jim Crow laws and segregation meant that black vacationers were often turned away from mainstream beaches and hotels. Oak Bluffs was the only town of the now six on Martha’s Vineyard where African-Americans were permitted to find lodging. Initially, freed slaves sought shelter there after slavery was abolished in the mid-19th century. Many worked in the fishing and whaling industry. Then, in the 1930s and ’40s, as African-Americans in urban centers like New York, Washington, D.C. and Boston began to take up jobs in professional industries and establish themselves as part of the middle and upper-middle class, they flocked to the East Coast shoreline in the summer to take in the beach and the bonfires. Today, Oak Bluffs, which sits on 7.4 square miles of land, maintains the charm of a fishing village with its colorful gingerbread cottages, pristine beaches, bustling marina and old-time seafood joints.
Left: Beachgoers enjoying themselves at Oak Bluffs in Martha’s Vineyard, 1950s. Right: People celebrating Memorial Day at Inkwell Beach, 2019.
Despite being an important historical haven for African-Americans, Oak Bluffs is not a majority-black town. The Martha’s Vineyard Commission reports that just 3.3 percent of Oak Bluffs’ full-time residents are black. But Oak Bluffs’ popularity as a summertime destination, particularly with African-American vacationers, means that the town’s population swells from 4,647 to 20,000 in a matter of weeks, a trend that year-round residents have coined “Black August,” and which drew hordes of news reporters to the island during the Obamas’ annual pilgrimages.
African-American identity is ingrained in the community, with luminaries such as Maya Angelou, Martin Luther King Jr. and Harry Belafonte having vacationed there. One of Oak Bluffs’ most popular hangouts, Inkwell Beach, pays homage to this history, its name a reference to beachgoers’ black skin, which was said to glisten like ink in the hot sun. The name is also a nod to the town’s rich literary history. Residents and vacationers gather at Inkwell to watch fireworks on the Fourth of July, spend the day digging for clams, and light up the shore with festive bonfires at night. Every morning, the Inkwell Polar Bears, a local swimming club, splash into the cold Atlantic waters just after sunrise, soaking up the earliest rays of summer.
Left: Family members outside an Oak Bluffs home, 1950s. Right: A neighborhood street in Oak Bluffs, 2019.
Abigail McGrath’s family has been summering in Oak Bluffs for six generations. “No specific things happen here,” she says. “You do the same thing over and over again. You always watch the fireworks, and you always go clam fishing.” McGrath descends from a line of notable literary elite who first arrived on the Vineyard in the 1930s. Her mother, Helene Johnson, was a Harlem Renaissance poet who socialized with the likes of author Zora Neale Hurston and celebrated African-American poet Langston Hughes in 1920s New York.
McGrath’s aunt, author Dorothy West, also owned a home in Oak Bluffs, where she became acquainted with Jacqueline Kennedy Onassis, who worked as an editor at Doubleday after her years in the White House. McGrath remembers peeking from behind the curtain and being awed at the sight of Jackie O. walking across her aunt’s front yard. Onassis edited West’s final novel, The Wedding, published in 1995 and set in 1950s Oak Bluffs, three years before West died. McGrath has since inherited her mother’s Georgian-style Oak Bluffs cottage, where she houses a writers’ residency in honor of her mother and aunt.
Left: Abigail McGrath at her home in Oak Bluffs. Right: Dorothy West’s family home.
“People have an impression of how Oak Bluffs is in July and August, but not a consciousness of a small town in which you know all your neighbors and where you read a book at night instead of watching TV,” says McGrath, who is in her late 70s and splits time between her homes in New York and Martha’s Vineyard. “Year-round people just want to go fishing in quiet and do a clambake and look at the stars. So, which party you’re invited to doesn’t mean as much to people who have been here for generations versus people who just got here.”
Oak Bluffs is essentially defined by its seasonal surge, and there are only two seasons that matter: summertime and the rest of the year. This divide also extends to the occasional friction between year-rounders and summertime vacationers. Twenty-two-year-old Avery Hazell, a college senior who grew up full-time in Oak Bluffs, says summer people are often immune to the tension.
“Some people in Oak Bluffs hold resentment toward the summertime vacationers because they don’t understand that this is where we live,” says Hazell. “We’re not hanging out and going to the beach. We work. This is our home. Sometimes there’s this sense that the summertime vacationers are taking over.”
Gates recalls a scene from last summer when acclaimed filmmaker Spike Lee threw a party at his home. Gates, who was at the party, used to work for Lee, and babysat his kids growing up. Droves of uninvited people crashed the soiree, and “it became this weird, ‘I need to be with Spike Lee’ vibe,” says Gates.
According to McGrath, “The fancy black people who come down here for the summer are the same as the fancy white people who come down here for the summer. They’re not residents. They simply summer here because it’s fun.”
But Gates, who admits her opinions are unpopular with some other residents, sees a more complicated transition in progress.
Distinctive gingerbread home details in Oak Bluffs.
“It’s not a safe place for a lot of the black community,” she says. “The community is angling itself toward ostracizing people from different classes, and there’s no greater weapon than internalized class division.”
Ironically, Gates appears nostalgic for a simpler Oak Bluffs that influential families like hers might have involuntarily helped to leave behind, as their connection to the town attracted others of similar means and social standing. Still, “It’s heartbreaking,” she says of the changes she sees. “In the ’90s it was cross-class, and I was in love with Martha’s Vineyard.”
Filmmaker Stanley Nelson, whose list of film subjects reads like a who’s who of black history — Miles Davis, Marcus Garvey, Emmett Till, Madam C.J. Walker, the Black Panthers, historically black colleges and universities — chose Oak Bluffs as the focus of his 2004 documentary A Place of Our Own. Nelson says that Oak Bluffs still plays an important role in providing a reprieve from the racism black people face on a constant basis. “Racism and prejudice still exists in this country, sometimes more so for successful people who have to be ensconced in all-white environments at work,” he says. “Oak Bluffs gives you a chance to let your guard down.”
Nelson, who is in his mid-60s, grew up summering in Oak Bluffs and still visits for several weeks each year.
“There’s a sense that this is a place where black people belong, a place where black people have a foothold,” he says. “People don’t look at you like, ‘What are you doing here?’ because black people have a place here.”
Oak Bluffs’ profile has risen with splashy, annual events that draw A-list crowds. The Martha’s Vineyard African-American Film Festival, coming up on its 17th summer, has featured appearances by cultural icons like Spike Lee and Barry Jenkins, the director and co-writer of the Oscar-winning Moonlight. And locals whisper about the annual White Party, an ornate garden party that doubles as a charity event, like it’s the holy grail of the summer social calendar. Not only has this contributed to some of the keeping-up-with-the-Joneses attitude that Gates describes, but it’s also resulted in a summertime population surge that presents a challenge for business owners.
“Our Christmastime is August,” says Roger Schilling, 55, who owns C’est La Vie gift shop on Circuit Avenue, Oak Bluffs’ main strip. “That’s it. We either make our money in August or we don’t.” Still, Schilling, who moved to Oak Bluffs from France in the ’80s with just $1,000 to his name, has only positive feelings about his decision. “In France, if you don’t come from money you can’t have money,” he says. “I came at the right time, the right place, and I’ve been very blessed.”
“We share the same love on the Vineyard,” Schilling adds. “The day I came here, I felt it. I’m living a life here I never thought I would. The sky’s the limit, that’s the beauty of America.”
Roger Schilling outside his gift shop, C’est La Vie. The store sits on Circuit Avenue, Oak Bluffs’s main strip. Schilling depends on summer tourists to make his living.
But with home prices inching over the half-a-million-dollars mark, Oak Bluffs has become inaccessible to many of the young people who used to be a mainstay on the Vineyard. The Martha’s Vineyard Planning Commission reports a median home price of $535,000 in Oak Bluffs, up from $135,000 in 1990; rent today averages between $1,600 a week for a summertime cottage and $11,500 a week for a luxury rental.
Danielle Hopkins, 19, who grew up full-time in Oak Bluffs and is now a sophomore at Barnard College, says the community could do more to increase job opportunities and affordable housing for young people. “You have to own a house to be able to live here,” Hopkins says. “There’s not very many apartment complexes. It’s very expensive. So you have to have a stable, wealthy job in order to live here.”
Danielle Hopkins grew up in Oak Bluffs and has seen how the neighborhood has become less accessible for the locals.
For Hopkins and teenagers like her who spend all year on the isolated island that is the Vineyard, life revolves around high school. Hopkins played field hockey, ran track, and campaigned for student council, when she wasn’t writing stories for the high school newspaper. “I did so much because I didn’t have anything else to do. I figured I might as well try things,” she says. In the off-season, when job prospects were scarce, Hopkins babysat, and like most teenagers on the Vineyard she balanced multiple summer jobs at restaurants. She says she feels lucky to have grown up in a community that celebrates African-American intellectuals, when society at large often doesn’t champion black people’s accomplishments.
Busy waiting tables, however, the elite vacationers were often just out of Hopkins’ reach. “I think it would be cool to hang out with the people who vacation here, but because I have work I never get to,” she says. “Sometimes I do feel a little removed, especially now that I’m in college. I feel connected to Oak Bluffs and Martha’s Vineyard, but I don’t feel like it’s a place where I belong.”
Fifty-five years after the Civil Rights Act of 1964, which marked the official end of racial segregation, other residents are grappling with a similar question, reflecting on the role that such a haven for African-Americans should play in today’s society. Despite the changes, culture clashes and ambivalence about the community’s future, Oak Bluffs still serves its purpose. It’s a refuge, year-round for some and seasonal for others, where black people don’t have to question their ability to congregate with one another, their drive or their capacity to succeed due to the color of their skin.
Left: A couple outside a home on Martha’s Vineyard, 1950s. Right: Antique home facades are common in Oak Bluffs.
Gates points to the time her father was arrested at his Cambridge, Massachusetts, house in the summer of 2009, as a result of what many believe to have been racial profiling. He had returned home after a business trip to find his door jammed, and a neighbor reported his attempted entry as a break-in.
“When we were in Oak Bluffs, it represented a safety net,” Gates says of the support the family received on the Vineyard at the time. “We had this black community that was so evidently vocal on our side. Because of how racially polarized we are now in America under Trump, people really feel worthless, so there’s this mentality of ‘at least I can afford to go to Martha’s Vineyard,’ and it becomes this mark of honor.”
“Black people want to feel worthy,” Gates adds. “We want to feel like we belong.”
Genelle Levy is a freelance culture writer who covers lifestyle, feminism, race, gender and the intersection between pop culture and social issues. She began her career as a contributing newspaper reporter in Syracuse, NY, covering local arts and culture before becoming an editor at Art+Auction. Currently as a freelance journalist her work has appeared in USA Today, TeenVogue, Bustle and Out Magazine. When she’s not writing, Genelle can be found reading, cooking or watching too many movies.