Preservation Vacation: Capturing the American Dream in Oak Bluffs

Posted on: December 28th, 2012 by David Robert Weible

Overton House, Oak Bluffs. Credit: Elaine Weintraub
Historic Overton House, Oak Bluffs.

Martha’s Vineyard. For me, the name alone conjures images of quaint port towns brimming with gingerbread houses, teak runabouts, and understated wealth of all manner -- a playground for the rich and powerful. And though you won’t have any trouble finding these things in Oak Bluffs, a small town on the island’s north shore, there’s more to the town than just the money. Since the early 1900s, Oak Bluffs has served as one of America’s premier African-American resort towns.

Originally, the town was the part of nearby Edgartown that was deemed a “suitable” place to live for the African-Americans who worked in the island’s laundries and hotels. In the early 20th century, these locals were joined by more affluent African-Americans who would come to be involved with the town’s Baptist revival activities, and a summer vacation spot was born.

“So by default really, Oak Bluffs becomes the place,” says Dr. Elaine Weintraub, board chair of the African-American Historical Trail of Martha’s Vineyard, “for young, educated, affluent, African-Americans -- the politicians and the movie stars.”

It’s a sentiment that’s still true today as political bigwigs like Valerie Jarrett frequent the town, while others have passed down property through generations.

Flying Horses Carousel detail. Credit: Paul Lowry, Flickr
Flying Horses Carousel detail.

Part of the reason for Oak Bluffs’ continued popularity is the fact that it’s never been an exclusively African-American town, Weintraub says. Today, the official U.S. Census will tell you that Oak Bluffs’ year-round population sits just under 4,000 and is more than 85% white.

"I don’t think there was an impetus [for African-Americans] to leave Oak Bluffs," Weintraub told me. "Why leave when it’s where you want to be and it’s integrated anyway?"

Visitors still flock to historic spots like the Flying Horses Carousel, said to be the oldest in the nation, and The Inkwell, the beach where African-American writers, politicians, and celebrities have swum for decades, including Dr. Martin Luther King, Jr., who made a habit of afternoon dips when staying at the nearby Overton House.

There’s also the Shearer Cottage, a traditional New England guest house with landscaped gardens that still sits just a few miles outside of town and housed some of Oak Bluffs’ most important visitors. It’s the oldest African-American-owned guest house on the island, and was the first to specifically cater to African-Americans, in 1903.

Overton House historical plaque. Credit: Elaine Weintraub
Marker for the Overton House.

Weintraub doesn’t anticipate much of a change in the foreseeable future for Oak Bluffs. She points to scores of summer symposia hosted by significant African-American intellectuals and the popularity of presentations by local librarians and historians as proof that the culture of Oak Bluffs seems as strong as ever.

“I think historically it has represented a place where African-Americans could be successful, could be around other African-Americans, could share in a culture and a place in the sun and that they’ll own and that they’ll belong,” she says. “When in most of the country you could not be what you were -- successful, upper middle class, striving for success, for the American dream -- Oak Bluffs represented freedom.”

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David Robert Weible

David Robert Weible

David Robert Weible is an assistant editor at Preservation magazine. He came to DC from Cleveland, Ohio, where he wrote for Sailing World and Outside magazines.

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