Island’s Heritage Trail honors African-American Vineyarders

Shearer Cottage is the first African-American-owned guest house on the Martha’s Vineyard.
Shearer Cottage is the first African-American-owned guest house on the Martha’s Vineyard.

OAK BLUFFS — Even into her 80s, Isabel Washington Powell wore high-heeled red sandals while entertaining her frequent guests in her summer home here. She called the house the “Bunny Cottage,” after the nicknames she and her husband, the congressman Adam Clayton Powell Jr., gave each other: Bunny Girl and Bunny Boy. Isabel maintained the summer home right up until her death at age 98, in 2007. The plaque that now marks the house includes a note about her famous Bloody Marys.

The Powells met when Isabel was dancing at the Cotton Club. They were married from 1933 until 1945, when Powell, a Baptist minister, left her for his second wife — another showgirl. The moral of her story, Isabel once told her friend Elaine Cawley Weintraub, was simple: “Don’t change yourself for anyone.”


Weintraub, a native of Ireland, might seem an unusual candidate to establish the Martha’s Vineyard African-American Heritage Trail, which began conducting tours almost 20 years ago. But as its cofounder, along with Carrie Camillo Tankard, vice president of the island’s NAACP chapter, she has overseen the steady growth of the tour from a humble, informal service showcasing a handful of notable homes, graves, and other points of interest, to a robust circuit of 27 sites and counting.

They span the island, from Chappaquiddick to Menemsha, marking the legacies of pastors, politicians, socialites, activists, a female boxing champion, a purported witch, and many more of the characters and community leaders who have graced the Vineyard’s long history as a summer retreat for some of the nation’s influential black families.

It’s quite a history. African-Americans have been living on Martha’s Vineyard since the 18th century, attracted by the jobs related to the island’s once-bustling whaling hub and the Baptist and Methodist revival meetings of the Oak Bluffs campgrounds, among other factors. By the turn of the 20th century, some homeowners had begun operating as innkeepers, drawing better-off black families from the cities of the Northeast and beyond for extended summer stays.


The Overton House, one of the stops along the Heritage Trail tour, is a Victorian seaside mansion once owned by a New York City labor leader. Sometimes called the “summer White House” of the civil rights movement, the sprawling inn hosted Harry Belafonte, Jesse Jackson, and many other notable figures over the years.

“It’d be easier to tell you who didn’t stay there,” Weintraub told a vanful of tour-takers on a gloriously sunny day last August.

One repeat guest at the Overton House, Dr. Martin Luther King Jr., spent his mornings on the porch overlooking the ocean, reading, and writing. That came as little surprise, said Weintraub. What did seem different, she continued, was the fact that he spent a few hours each afternoon frolicking in the water.

“Heroes don’t go to the beach,” she joked.

The beach in Oak Bluffs is known as the Inkwell. The name likely had negative connotations: it’s said (though no one seems to know for sure) to have been coined by white islanders who disparaged its mostly black habitues. Today, however, it’s a source of pride.

The first stop on the tour is usually the Shearer Cottage, a pretty red compound located in the woods of the Highlands of East Chop. The family of Charles and Henrietta Shearer, who were drawn to the island for its Baptist revival meetings, established a guest house on their grounds more than a century ago. The tour guides like to tell their audiences about the wedding that took place at the cottage in the 1970s, when Lionel Richie and the Commodores performed in the driveway.


Weintraub taught history at Martha’s Vineyard Regional High School, including courses on Irish and Brazilian heritage, until last year. The growing African-American Heritage Trail tours now have three drivers who are her former students, she says: “It’s coming full circle.”

The tours now operate several times a day, with options ranging from 90 minutes to 4½ hours, most days through September. Groups are also accommodated by request. Repeat visitors are common: last summer, US Representative Barbara Lee booked a group tour for the fifth time.

Unsurprisingly, the Obama family’s recent summer visits to the island have been good for business, Weintraub says. On the tour I took last August, the van slowed in beach traffic as it passed alongside Farm Neck Golf Club.

“I wonder if Obama is golfing today?” mused the tour guide.

After the Heritage Trail dedicated a plaque to the summer home of Ed Brooke, the longtime Massachusetts politician who was the first African-American popularly elected to the Senate, Weintraub was introduced to the former senator.

She asked how it felt to establish so many “firsts”: first black attorney general of a state, first to integrate certain hotels, and so on.

“I have to tell you,” he said. “It made me very tired.”


But he came back each summer to the Vineyard, to recharge.

James Sullivan can be reached at jamesgsullivan@gmail.com. Follow him on Twitter @sullivanjames.