An African-American resort area that’s more than 125 years old, Oak Bluffs has earned its seat at history’s table. Black families stay all over the island now, huddling over lobster rolls or fried clams from Chilmark to Edgartown, but that was not always the case. “Oak Bluffs,” Dr. Harris said, “was the hub of the island’s black life.”

The front porch of Shearer Cottage, the kitchen of which Ebony magazine praised in 1963 for its “fine foods.” Now, instead of a main dining hall, the cottage provides kitchenettes in each of its six studios. The community is showcased in an exhibition at the National Museum of African American History and Culture called “Power of Place.” But the common labeling of homeowners and regular visitors there as “the elite” leaves out the social nuances.

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.