The fact is, strivers are responsible for making Oak Bluffs a destination: Formerly enslaved people, or their descendants, bought property around Baptist Temple Park in the early 20th century, drawn by the religious services held there. Teachers, politicians, lawyers, doctors, artists, musicians and entrepreneurs all arrived and flourished for decades afterward.
This summer was my seventh on the island, and I was itching for a proper tour of the African-American Oak Bluffs.
I met Abigail McGrath, the founder of Renaissance House writer’s retreat, and the daughter of the poet Helene Johnson. Ms. McGrath invited me to hop in her truck, and we circled the Highlands area of Oak Bluffs, where almost every facade has a quarter board listing the household name. We cruised past the Oval, the grassy park where Dorothy West, Ms. McGrath’s aunt, set her 1995 novel, “The Wedding.” It’s across from the Bunny Cottage, once home to Adam Clayton Powell Jr., the congressman from Harlem, and his first wife, Isabel.
We reached a large round stone marked “Shearer,” announcing the inn founded by Henrietta and Charles Shearer, who had attended the school now called Hampton University and then moved to Boston, where Charles was the headwaiter at the Parker House Hotel.
The cottage was their summer home starting in 1903; accommodations were added in 1912, along with a dining room, where Parker House rolls were present at all meals. In the 1963 edition of Ebony magazine’s vacation guide, the Shearer Cottage listing speaks of its fine foods.
Inside the inn, the brightest minds congregated for breakfast at small tables covered over with pancakes, bacon, sausage, fish cakes, hominy. Or they might have made reservations for dinner, said Lee Jackson Van Allen, the current owner and innkeeper, and a great-granddaughter of Henrietta and Charles. The dining room closed in the 1970s, but in its day you’d rub elbows there with African-American luminaries: the singer and composer Harry T. Burleigh, the entrepreneur and philanthropist Madam C. J. Walker, the actors and singers Paul Robeson and Ethel Waters.
“My great-grandparents were born in Virginia, and the food was very much Southern: macaroni and cheese, peach cobbler and candied sweet potatoes,” Ms. Van Allen said. “Everything was always very fresh — they went to the market every day.”
Daylight was fading. To fully experience the Vineyard vibe, a barbecue or clambake invitation is needed. Sometimes, frying scup (better known as porgy) and lingering for hours at home happens, too.
But Dr. Harris was hosting a porch party: a throwback Vineyard “five to seven,” a post-sunbathing social that marks the beginning of dusk. Some say the two-hour function died out decades ago, but her dainty white linen napkins, stacked alongside antique dishes filled with local cheeses, said otherwise.
I met Martha Mae Jones, an artist who has been coming to the island for more than 35 years. “There’s something called Vineyard magic,” she said. “You’ll always meet someone from across the country that is connected to you.” Crisp bubbly wine flowed; new bonds were forged.
After a week of up-island farm stand-hopping and West Tisbury farmers’ market-shopping, I felt like a bona fide seasonal dweller. My gray shingled rental house had an outdoor drop-leaf table, and I arranged platters of herb-rubbed grilled tuna and Southern succotash. It was the inaugural visit for my Brooklyn and Atlanta friends. They arrived and asked, “What makes the place so special?” The recipe is a secret.