From New York Magazine on the Obamas’ possible summer plans in a wealthy Liberal bastion of non-racial intermingling:
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.”