The rumors that the Obamas will be vacationing on Martha’s Vineyard this summer have been spreading since April. Locals are famously ho-hum about these kinds of things, but even they admit that this could be an unusually crowded August on the island, with three sets of Democratic Party royalty descending at once.
The Clintons are expected to return to Edgartown, where they have often stayed at the home of Richard Friedman, a Boston real-estate developer. Caroline Kennedy will be at her mother’s former estate in Aquinnah. And while the Obamas’ plans are still unannounced, most people expect the First Family to settle on Oak Bluffs, at the northeast end of Martha’s Vineyard.
A few Vineyarders say they know whose home it’ll be. “The rumor is that it’s Wayne Budd,” says one, referring to the prominent Boston lawyer who was associate U.S. attorney general under the first President Bush. “He has a very large house with guesthouses that would be perfect for the Secret Service and his staff.” Budd has denied this, and a wealthy friend of the Obamas who claims to have been provided a photo of the chosen house says that the Oak Bluffs rumor is wrong. “The picture I received looks like it could be West Chop,” this friend says, referring to a neighborhood across the harbor. “But West Chop is totally white—so totally white that it would be a surprise.”
Even if the Obamas do choose West Chop, they’ll surely spend considerable time in Oak Bluffs, a town known for attracting most of the upper-class black professionals who stay on the island. As liberal as it is, the Vineyard is about as racially integrated as a college dining hall—blacks and whites get along fine, but they generally don’t socialize. “There’s not a lot of overlap between black and white,” says radio executive Skip Finley, who started vacationing in Oak Bluffs in 1954 and has been living there full-time for the past decade. “I don’t think anybody’s insulted by it. I’m certainly not.” It’s an arrangement that springs largely from the self-segregating impulse among black Vineyarders, who have come to the island to connect with each other. “We have people here who are black and upscale and racist,” Finley continues. “They don’t want to be around white folks, and they don’t have to.” By choosing to vacation in and around Oak Bluffs, the Obamas would be throwing a spotlight on one of the most demographically unusual towns in America.
In 1912, a former slave named Charles Shearer opened the first summer inn in Oak Bluffs that catered specifically to black patrons. Only a few dozen blacks visited the island at the time, but over the years Oak Bluffs has become the summer meeting place for scores of what could be called the Only Ones—black professional and social elites who travel in worlds where they’re often the only black person in the room. The Only Ones typically break into fields or companies that admit few blacks, move into neighborhoods where few blacks live, and send their kids to mostly white schools. They are not running from their own—they’re chasing after the best they can get. They aren’t assimilationist; they’re ascensionist.
Senator Edward Brooke, Congressman Adam Clayton Powell Jr., Ethel Waters, Paul Robeson, and Dr. Martin Luther King Jr. all made visits to Oak Bluffs. The novelist Dorothy West moved to the island in the forties, working for the Vineyard Gazette first as a file clerk and then, for decades, as a columnist who wrote about the prominent blacks visiting the island. Today’s summer vacationers come from the worlds of academia (like Harvard professors Skip Gates, Charles Ogletree, and Lani Guinier), media (NPR correspondent Charlayne Hunter-Gault, former ABC News anchor Carole Simpson), film (directors Spike Lee and Reggie Hudlin), and politics (Valerie Jarrett, who hosted the Obamas in 2007). “If you’re upper-middle class and black, this is your spot,” Finley says. “You’re going to find a way to spend a little bit of quality time here on this island.” In Oak Bluffs, the Only Ones become one of many. “I went to a garden party last weekend,” Simpson says, “and you would not believe the occupations of the people I met there. It’s like all the African-American East Coast professionals have chosen this place to socialize with each other.”
Not all blacks stay in Oak Bluffs; Vernon Jordan lives about fifteen miles away, in Chilmark. And the social scene in Oak Bluffs doesn’t exclude white islanders. Craig Hockmeyer, who owns a bicycle shop in nearby Vineyard Haven, says he spent many nights at Lola’s, which was, until its recent closing, a central part of the Vineyard black universe. “A bald white honky like me could go in there and feel totally comfortable and dance the night away with all the rich black folks, not a problem at all.” Still, Vineyard whites understand that blacks in Oak Bluffs take their socializing seriously. “I think the African-American summer community is more active in terms of the social network,” says Ron Mechur, a local real-estate appraiser. “They do more things, host more affairs, and support one another as friends. The white community doesn’t do as much, and they’re not as connected.”