Beautiful beaches and coastal towns are only part of the story. For generations, Martha's Vineyard—especially Oak Bluffs—has held a distinctive place in Black American history, culture, community, and summer tradition.
Watch First
See why Martha's Vineyard feels different
Start with this short video for a quick feel for the island, then explore the history, people, places, and traditions that make this such a meaningful destination.
First, the basics
What is Martha's Vineyard?
Martha's Vineyard is an island about seven miles off the Massachusetts coast. It has six towns, more than 124 miles of tidal shoreline, and large areas of protected land. There are beaches, harbors, lighthouses, bike paths, galleries, restaurants, historic villages, and dramatic coastal scenery.
The Wampanoag called the island Noepe, often translated as “land between the streams.” The Wampanoag people have lived here for thousands of years, and the Wampanoag Tribe of Gay Head (Aquinnah) remains an important part of the island today.
A special Black American legacy
Oak Bluffs is more than a beach town.
Black history on Martha's Vineyard reaches back centuries. By the 19th and early 20th centuries, Oak Bluffs had become a place where Black families could vacation, own homes, build businesses, worship, socialize, and create community at a time when segregation sharply limited where Black Americans were welcomed elsewhere.
That tradition became multigenerational. Black teachers, doctors, lawyers, artists, writers, politicians, entrepreneurs, and families returned summer after summer. Today, Oak Bluffs remains one of America's best-known historic Black summer communities.
A landmark story
Shearer Cottage
Shearer Cottage became the island's first African American-owned inn serving Black vacationers. It offered something profoundly important in the era of segregation: a welcoming place for Black travelers to stay and gather. Its guests included Madame C.J. Walker, Paul Robeson, Ethel Waters, and opera singer Lillian Evanti.
Walk through the history
African American Heritage Trail
The African American Heritage Trail of Martha's Vineyard now identifies more than 30 sites across the island connected to people of African descent. Sites include homes, churches, community landmarks, Shearer Cottage, the Powell Cottage, the Overton House, and places connected to Black maritime, religious, political, and civic history.
Names you may recognize
Presidents, civil-rights leaders, artists & icons
The Vineyard's story includes an extraordinary list of visitors, residents, and summer regulars. President Barack Obama and his family vacationed on Martha's Vineyard before and during his presidency. Historic records and local heritage sources also connect the island with figures including:
Martin Luther King Jr.Coretta Scott KingMalcolm XJackie RobinsonMadame C.J. WalkerPaul RobesonEthel WatersAdam Clayton Powell Jr.Edward BrookeDiana RossLionel Richie & the CommodoresDorothy West
Some were residents or regular summer visitors; others are documented historic guests or visitors. Their relationships to the island were not all the same.
The Inkwell
A beach with cultural meaning
Inkwell Beach is a small Oak Bluffs beach, but its meaning is much larger than its size. Generations of Black families have gathered there, making it part of the social and cultural fabric of the Black summer experience on the Vineyard. It is also where Trina's notes place beach yoga and the morning Polar Bears tradition.
Beyond Oak Bluffs
Six towns. Very different experiences.
Oak Bluffs brings colorful gingerbread cottages, beaches, history, shops, restaurants, and an energetic harbor. Edgartown offers classic New England architecture and waterfront charm. Vineyard Haven has a working harbor, shopping, and galleries. Aquinnah is known for its dramatic clay cliffs, lighthouse, and Wampanoag culture. Chilmark and West Tisbury offer a quieter, more rural side of island life.
Why make this trip?
This isn't just a place to visit. It's a place to experience together.
You can spend the morning on a beach that generations of Black families have loved, walk through nationally significant Black history in the afternoon, dress up for dinner, attend a film or cultural event, watch the sun set over the water, and still have completely different experiences waiting the next day.
For Trina's milestone trip, that combination matters: beauty, history, Black culture, relaxation, fun, and time together. The trip is not about checking attractions off a list. It is about having enough time on the island to settle in, explore, enjoy the island, and make memories with people you care about.
More to Watch
Get a little more of the Vineyard before you go
These are the other Martha's Vineyard videos from Trina's original planning notes.
Martha's Vineyard Video
One of the short videos Trina saved while planning the trip.
More Martha's Vineyard
A longer video from Trina's original trip-planning document.