Shearer Cottage and the Rich African American Heritage of Martha’s Vineyard
Sunshine, sailing, and gingerbread cottages covered with whimsical detailing. The town of Oak Bluffs on the north end of Martha’s Vineyard, a port of entry for many summer vacationers, is defined by these qualities. But sometimes left out of its definition is Oak Bluffs’ historical status as a popular destination for the African American elite, musicians, and politicians alike. And an essential part of that is Shearer Cottage, the oldest African American-owned inn on the island.
“It’s really a story of family strength,” says historian Elaine Cawley Weintraub. Cawley Weintraub created the African American Heritage Trail of Martha’s Vineyard in 1998, leading tours and telling the stories of the island’s rich heritage. The first stop on the tour? Shearer Cottage.
The story behind the cottage, which was listed in the Negro Motorist Green Book as a safe place for African American travelers to stay, is a major reason why Cawley Weintraub selected it. Charles Shearer was born to an enslaved woman and a white farm owner in 1854. When Union soldiers arrived at his birthplace in Appomattox County, Virginia, during the Civil War, they allowed Shearer to accompany them. Though he never fought in the war, Shearer’s knowledge of the region and hunting skills made him a valuable resource for the troops.
After the war ended, Shearer enrolled at Hampton Institute (now Hampton University) in Virginia. He eventually became a professor at the college and met his wife Henrietta, also a teacher. The couple moved northward to Massachusetts around 1877 and purchased a property on Martha’s Vineyard, where a vibrant African American community had emerged.As long as European Americans have populated the island, so too have African Americans. Some came as indentured servants or fleeing slavery. The booming whaling industry also drew people searching for reliable employment (whale oil being an essential energy source). By the time Ted Kennedy and the Chappaquiddick incident brought the island greater notoriety in the late 1960s, many plots had been owned by African American families for generations. Property ownership led to a greater sense of community ownership, Cawley Weintraub says. The land was theirs, and it was their responsibility to make it a place worth staying.
Back in 1912, the Shearers sensed a business opportunity in this budding community. What if they opened an inn catering specifically to African Americans? After all, African Americans were not welcome at any other lodging on the island. Though Henrietta had run a successful laundry for the preceding ten years, the Shearers took the plunge, building a 12-room wooden cottage on part of their property.
Within a matter of years, Shearer Cottage had become an Oak Bluffs establishment for serial renters and year-round residents alike. It was so frequently overfilled with guests that the Shearers asked nearby houses to provide sleeping arrangements for the room-less, and upwards of 50 people would gather in its dining room to enjoy communal meals.
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A “who’s who” of prominent African Americans steadily streamed into the cottage throughout the decades. Madame C.J. Walker, singer and activist Paul Robeson, actress Ethel Waters, and opera singer Lillian Evanti all stayed there. Adam Clayton Powell, Jr., New York’s first representative in Congress of African American descent, regularly summered at the cottage during his childhood. And Lionel Richie and the Commodores, who were managed for a time by a third-generation Shearer, spent summers there honing their craft. “There weren’t many places African Americans could stay, no matter how famous and talented you were,” Cawley Weintraub says. “So a place like Shearer was extremely important and well-known by African Americans."
But when Cawley Weintraub arrived in Martha’s Vineyard in the late 1980s, she was shocked to find that Shearer Cottage and the history of African Americans had been largely left out of the island’s narrative. She taught at a school in Oak Bluffs and found herself wanting answers when students asked about the island’s African American history.
“I remember thinking, ‘Someone must have written about it,’” says Cawley Weintraub. “I took it for granted that it had been covered, but it hadn’t.”
Motivated by her mission to “record and celebrate” these untold stories, Cawley Weintraub teamed up with activist Carrie Tankard to found the African American Heritage Trail. They spent months poring through archives and interviewing people with deep ties to the neighborhood. Their research turned up photographs and letters from Charles Shearer, helping them build a more definitive timeline of events and offering insights into Shearer’s character. For example, an 1898 handwritten letter to a friend reasserts Shearer’s appreciation for his alma mater. “I find without the useful training received at Hampton [Institute], I would have failed in many instances," he writes.
Tankard and Cawley Weintraub initially hoped to include four sites on the trail. Today, that number has grown to 27 sites and counting.
Each site is dedicated in a ceremony, with the unveiling of a plaque for passersby to learn of its significance. In 2018, four places were dedicated. Among the newest additions are the Jennings Family Home, the home of the first African American to graduate from Hartford Hospital School of Nursing in Connecticut, and the Dukes County Courthouse, which has served Oak Bluffs and surrounding towns since 1858. Tours of the Heritage Trail sites run from May through Labor Day.
Meanwhile, life at Shearer Cottage continues much as it always did. It remains in the possession of Shearer’s descendants, carefully preserved and maintained throughout the years. Some of its artifacts even reside in the collection of the National Museum of African American History and Culture in Washington, D.C., including a wooden sign and a wicker rocking chair. And though it sits only a few minutes’ walk from downtown Oak Bluffs, which remains as animated as ever, Shearer Cottage can feel a world away.
“[Oak Bluffs] is the town with the summer razzmatazz. The liveliest town, I guess,” Cawley Weintraub says. “But if you were sitting in a rocking chair on the cottage’s porch, you’d think you were miles away from all that activity. It’s very peaceful.”
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