Martha’s Vineyard is a summer destination known for its history, its beauty, and in recent decades, its strong Black presence. In Oak Bluffs, you’ll find generations of Black families, celebrities, and first-time visitors all gathering in August to rest, reconnect, and enjoy the island at its liveliest. It’s part tradition, part community, and fully intentional.
You’ve probably heard about the Vineyard—maybe for the Obamas, the lobster rolls, or that house your friend’s bougie aunt has rented since the ’80s. But there’s more to the island than what makes it into conversation. Especially in late summer.
If you want more Black history, check out our article about Juneteenth and Black Dandyism.
Where Is Martha’s Vineyard?
Martha’s Vineyard is an island off the coast of Massachusetts. It’s part of New England and only accessible by ferry or small plane. Most people arrive on the Steamship Authority ferry from Falmouth. You can bring a car, but reservations fill up fast in August. Small regional flights to the island are also available.
August is the busiest time to visit. The island is full of events, tradition, and visitors. For a quieter trip, try June or September. The weather is still warm, and the pace is more relaxed.
There aren’t many chain hotels on the island, so most people rent a house—sometimes with friends or extended family. Planning ahead is key, since accommodations fill up quickly and prices jump during the summer months.
How did Martha’s Vineyard Get Its Name?
The name “Martha’s Vineyard” dates back to the early 1600s, given by English explorer Bartholomew Gosnold. Historians believe he named it after either his daughter or his mother-in-law. It’s not clear which Martha he had in mind. There weren’t any real vineyards on the island. He likely saw wild vines and assumed they produced grapes.
The island has long been a vacation spot for wealthy East Coasters. Over time, its appeal to Black visitors—especially in August—has taken on a unique cultural and historical significance.
Fun fact: growing up, I thought Martha’s Vineyard was owned by Martha Stewart. Kid logic, y’all.
The Settler History of Martha’s Vineyard & Native Erasure
Before it was ever called Martha’s Vineyard, the island was known as Noepe, or “land between the streams,” by the Wampanoag people who lived there for thousands of years. The Chappaquiddick and Aquinnah communities hunted, fished, farmed, and traded across the region long before any ferry or vacation home showed up. Their connection to the land was deep, seasonal, and intentional.
When English settlers arrived in the 1600s, that way of life was disrupted. Like so many other parts of New England, colonization meant stolen land, forced displacement, and generations of erasure. But the Wampanoag people are still there.
The Chappaquiddick Wampanoag continue to live on the island today, though they don’t have federally recognized land. They’ve been pushing for reparations and formal recognition. Their sister tribe, the Aquinnah Wampanoag, gained federal recognition in 1987 and have land in the town of Aquinnah, at the western tip of the island.
Every July, the Chappaquiddick Wampanoag gather on their ancestral land to celebrate their culture and community. Once numbering in the thousands, there are now an estimated 300 Wampanoag people still living on what is now called Martha’s Vineyard.
The Legacy of Oak Bluffs: A Historically Black Haven
Oak Bluffs, on the northern side of the island, is where you’ll find the most concentrated and historic Black presence. The town has long been a place of refuge and community for Black Americans—but that legacy exists alongside a more complicated history.
In the 1600s and 1700s, Black people—both enslaved and free—lived and worked on Martha’s Vineyard. Some were brought to the island through slavery, while others worked as sailors, whalers, or domestic laborers. Though Massachusetts abolished slavery in the late 1700s, the legacy of Black labor is deeply embedded in the island’s early economy.
By the 1800s, Martha’s Vineyard also became part of the Underground Railroad’s maritime route. The island offered shelter to freedom seekers like John Thompson who escaped by sea. That spirit of protection and possibility continued into the late 1800s and early 1900s.
Black families began building vacation homes in the area. The gingerbread cottages, arcades, and beach scene made it feel welcoming. At the time, much of the country was still deeply segregated.
In 1912, Charles Shearer, the son of a formerly enslaved man, opened Shearer Cottage. It was one of the first inns on the island to welcome Black travelers. Over the years, guests included Adam Clayton Powell Jr., Paul Robeson, Madam C.J. Walker, and Harlem Renaissance writer Dorothy West.
Shearer Cottage was later recognized as the first stop on the African American Heritage Trail of Martha’s Vineyard. The trail was founded in 1998 and now includes over 30 sites honoring the contributions of Black residents and visitors to the island’s history.
The Inkwell Beach & Martha’s Vineyard Polar Bears
Inkwell Beach, located in Oak Bluffs, was once given its name as a slur. Some say the term came from the dark seaweed in the water, but many agree it was also a reference to the skin color of the Black beachgoers who gathered there. Over time, the name was reclaimed, and today Inkwell Beach stands as a proud symbol of Black presence on the island.
One of its most cherished traditions is the Polar Bear Swim, a daily gathering that takes place every morning at 7:30 a.m. from July 4th through Labor Day. The group, made up mostly of Black women, spans generations and was originally formed in 1946 by Black workers who used their only free time—early mornings—to swim together before their shifts.
Myrtle O’Brien, a Black innkeeper on Martha’s Vineyard who owned two properties, gave the group its name. What started as a morning ritual among co-workers became a beloved tradition rooted in wellness, community, and joy.
“It’s something about starting your day in the ocean, which I think is an extreme blessing… We love being Polar Bears.” – Caroline Hunter, longtime member and organizer
The August Migration: Black Wealth, Visibility, and Celebration
August is peak season in Martha’s Vineyard, and for many Black families—especially those in the upper middle class and elite—it’s an annual tradition. Writers, politicians, judges, academics, and celebrities all make their way to Oak Bluffs and the surrounding areas. Some Black families have been summering there for generations, while others rent homes with friends or attend annual events.
Events like the Martha’s Vineyard African American Film Festival and parties at places like Nomans are major draws. Black-owned businesses flourish during this time, including Biscuits, Fat Ronnie’s, Donovan’s Reef (frozen cocktails right next to Nancy’s), Caleen’s Spa, and C’est La Vie, a boutique shop on Circuit Avenue.
Martha’s Vineyard in Pop Culture
The Vineyard has shown up in both politics and pop culture. The Obamas famously vacation there. Sasha Obama even worked at Nancy’s, a popular seafood spot. But the island has also served as a backdrop for several Black-led stories on screen.
- The Inkwell (1994): A coming-of-age film starring Larenz Tate and Jada Pinkett, set during the summer of 1976. Tate plays a shy teen spending time with his wealthy relatives on the island. The film’s name references Inkwell Beach, a historic gathering spot for Black beachgoers.
- Jumping the Broom (2011): This romantic comedy follows a wedding between two Black families—one wealthy, one working-class—set at a beachfront estate on the island. It explores class tension, family drama, and tradition.
- Our Kind of People (2021): A Fox drama starring Yaya DaCosta as a single mom who moves to Oak Bluffs to grow her hair-care business. She steps into a world of legacy, secrets, and Black affluence.
- Summer House: Martha’s Vineyard (2023): This short-lived Bravo reality show followed a group of young Black professionals vacationing in Oak Bluffs. It highlighted friendship, drama, and Black property ownership on the island.
- Bel-Air (2024): In the season 3 finale of the Fresh Prince reboot, Hilary Banks’s wedding takes place on the Vineyard, reuniting the show’s characters for a big family moment.
- Forever (2025): In Netflix’s modern adaptation of Judy Blume’s novel, episode 5 takes place on the Vineyard. Directed by showrunner Mara Brock Akil, it follows two teens reconnecting with family. Akil, a part-time resident, used the episode to honor the island’s meaning in Black culture.
Housing Crisis on the Vineyard
While visitors enjoy lobster rolls and beach days, islanders—especially working-class residents—face growing housing insecurity. According to a 2006 Martha’s Vineyard Commission study, the cost of living is 60% above the national average and housing prices are 96% higher, even as median wages remain 71% of the Massachusetts average. As of 2023, the typical home on MV sells for around $2.3 million.
Harbor Homes, the island’s only formal shelter provider, operates a winter-only facility—open November through mid-April—with up to 25 beds. In the summer, however, their shelter doors close, and homeless residents are left seeking shelter in tents, cars, or state forest encampments—until outreach teams step in with food, supplies, and medical support.
A recent 2025 count found 60–88 unhoused individuals during the winter shelter season, with as many as 150 living without stable housing during summer months. Many of those affected are working—retail workers, service staff, and even educators—caught in the seasonal “island shuffle” of unaffordable rent.
Efforts are underway to address the crisis: Harbor Homes runs winter shelter programs, transitional congregate housing, a summer outreach program, and a hotel respite initiative for medically vulnerable residents. However, the lack of a permanent, year‑round facility remains a major gap. Ongoing zoning challenges, Not In My Backyard (NIMBY) pushback, and prohibitive real estate costs continue to block progress.
Before You Visit Martha’s Vineyard
You’ll need to plan ahead. In peak season, even restaurant reservations can be hard to come by.
Before you book your ferry or flight, know the legacy of the land beneath your beach chair. Martha’s Vineyard is more than a vacation spot. It holds history, community, and a lot of work happening behind the scenes to keep it livable for the people who call it home year-round.
If this kind of trip is within your budget, think about setting aside something for the people who’ve been here the longest. That might look like supporting Black-owned businesses, contributing to Wampanoag cultural efforts, or donating to Harbor Homes, the island’s only shelter.
