For Black Women, Saying Goodbye to Martha’s Vineyard Gets Harder Every Summer

I've been going to Martha's Vineyard for almost a decade. My first introduction to the island was through my mother, who's been visiting for over 20 years. She started going in her 30s, when a woman from our church would host an annual girls' trip. Year after year, she returned on the ferry, building friendships, traditions, and memories in a place that offered something she didn't often find elsewhere: the freedom to simply exist, surrounded by other Black people doing the same.

Years later, when I was old enough to experience the Vineyard for myself, that same woman who had first welcomed my mother to the island welcomed me. In some ways, it felt like a coming of age, and specifically, a coming into womanhood. I was being welcomed into a tradition that existed long before me — one that had been passed from one generation of Black women to the next. From the time I arrived, I understood without a doubt why my mother kept returning. And now, every year, we return together as a family.

But our story isn't unique. For generations, Black families have returned to the Vineyard, and Black women in particular have found something there that can be difficult to find elsewhere: belonging and rest among people who look like us. But that sense of belonging didn't appear overnight.

Black people have been part of Martha's Vineyard's story for centuries. The earliest documented Black residents on the island included enslaved Africans in the 1700s, and records later show Black Islanders working in homes and throughout the island's maritime economy as sailors, cooks, sailmakers, fishermen and whalers. After slavery ended in Massachusetts in 1783, free Black people continued to build lives on the Vineyard, including through fishing and whaling, while some established roots and became property owners.

By the 19th century, the Vineyard had become a place where Black families and visitors traveled from across the country to vacation there. And as the island developed into a summer destination, Black residents and visitors continued creating intentional communities of their own, specifically in Oak Bluffs. At a time when segregation and discriminatory practices restricted where Black Americans could vacation, stay and purchase property, Oak Bluffs was a town where Black people could buy homes. And because Black travelers could not count on being welcomed at hotels and inns across Martha's Vineyard, Black homeowners and business owners created places for other Black visitors to stay.

That access to property did more than create a vacation destination. It allowed us to put down roots on this little island off the coast of New England. Black families bought homes, welcomed friends and relatives, and returned summer after summer, creating traditions that could be passed from one generation to the next. Over time, Oak Bluffs became the center of a thriving Black summer community, one that drew generations of Black families, as well as some of the most prominent Black artists, writers and leaders of their time, including Dr. Martin Luther King Jr., Harry Belafonte and Maya Angelou, who once described the Vineyard as "a safe place where we can go as we are and not be questioned."

That tradition continues today. Barack and Michelle Obama have a home on the Vineyard where they spend every August, alongside a new generation of familiar faces like Gabrielle Union and Dwyane Wade, Spike Lee, Tina Knowles and Tracee Ellis Ross. In many ways, Martha's Vineyard became a third space in vacation from a place outside of home and work where generations of Black people could return, gather and simply be. And Oak Bluffs was at the center of it. The traditions, community, and emotions that have been fostered here over the years are what keep generations of Black families, and more specifically Black women, coming back.

"I came to Martha's Vineyard 38 years ago and got welcomed by the Polar Bear[s]," says Caroline Hunter. The 80- year-old tradition began at the Inkwell in 1946 when two Black sisters, known as the O'Brien sisters, purchased a cottage in the Campgrounds and moved it to the end of Circuit Avenue, where they operated it as a bed-and-breakfast. Nine Black guests who had come to the Vineyard for summer work began swimming together early in the morning, when their work schedules allowed. What started as a morning swim among a small group would grow into an eight-decade tradition of exercise and fellowship.

Today, from July 4 through Labor Day, the Polar Bears still meet at the Inkwell at 7:30 each morning for an hour in the water. "I got hooked, because I looked at these women, I was in my late 30s, and they were in their 60s, 70s and 80s," Hunter says. "The kind of quality of life, and an uprightness and an energy that, to me, was very exciting. So I was like, 'I've got to be with these old people, because they got something going on.' And as life changed and they got older, myself and another lady took it over."

Nearly four decades later, Hunter she is helping carry that tradition forward as a Polar Bear leader. For her the tradition and the vineyard as a whole is rooted in wellness. "Lots of beautiful things happen when people do things collectively," she says "That's the true meaning of community and wellness. When people live on an island, they have a different sense of community, connectedness. As someone approaching my own 10th summer as a Polar Bear, I asked Hunter what women of my generation can do to preserve what women like her have built. Her answer was simple: take up the mantle.

She wants the next generation to understand that inheriting these spaces comes with a responsibility to show up, to care for one another, and, above all, to be responsible and kind.

Erin Goldson knows something about taking up that mantle. The founder and CEO of Vineyard Icon comes from a family whose relationship with Martha's Vineyard spans five generations. That history begins with her great-grandmother, Lucille Lipman, who emigrated from Kingston, Jamaica, to Boston at 13 and purchased a home on Tuckernuck Avenue in Oak Bluffs in 1946.

"What I love about her story is that she did not simply buy a house. She built a community around it," Goldson says. "She rented rooms, welcomed friends and visitors from places like Boston and New York, and introduced other families to the Vineyard who eventually became homeowners themselves."

Lipman became a founding member of The Cottagers, a nonprofit organization of Black women homeowners on Martha's Vineyard. And the intentional roots she planted have extended through five generations of Goldson's family. Her parents met on the Vineyard when her mother was 17 and later married there. Her sister was married there in their mother's wedding dress. Her grandmother, who lives on the island year-round, turns 100 this year and was one of the happiest attendees of Goldson's Vineyard Icon Awards this year.

"So when I say Martha's Vineyard is home, I really mean it," Goldson says. "It has held almost every chapter of our family's story." Goldson has never missed a summer on the Vineyard.

"I remember being in middle school and realizing that I almost lived two parallel lives," she says. "During the school year, I attended a predominantly white private school in Washington, DC. Then summer would come, we would pack our family car to the roof, and I would arrive on the Vineyard surrounded by Black excellence across generations."

At the time, she didn't yet have language for what made that experience so significant. "I just knew that I felt safe, known, and free," Goldson says. "I could ride my bike to the Inkwell, watch the Polar Bears in the morning, walk around town, work different summer jobs, and move from one friend's house to another." The freedom that Goldson describes on the Vineyard, still exists, as so much of what many people discuss about Martha's Vineyard is how safe they feel, and how their children are the freest they've ever been when on the island. "I felt independent, but I was never really alone," she says. "Friends, relatives, and neighbors were always nearby and looking out for me. There were people who had known me, my parents, or my grandparents for years."

But that freedom she feels here, she was taught by the many in her family, was a privilege that she shouldn't take for granted. "You do not simply inherit a place like this," Goldson says. "You have a responsibility to care for it, contribute to it, and leave something meaningful for the people coming behind you." Goldson says that responsibility was part of what led her to create Vineyard Icon, which celebrates people who have contributed to the island while giving back to the community through local organizations and scholarships.

"The celebration matters, but so does the responsibility that comes with it," she says. And when I asked Goldson whether describing Martha's Vineyard as a refuge for Black women matched her own experience, she didn't hesitate.

"Absolutely. To me a refuge is a place where you can put some of the weight of life down and return to yourself — a place where you can exhale," she says. "Black women spend so much of our lives navigating spaces where there is pressure to perform, achieve, explain ourselves, or represent something larger than ourselves. On the island you can see incredibly accomplished Black women riding bikes, sitting on the beach, walking down Circuit Avenue, having coffee with friends, or sitting on a porch doing absolutely nothing," Goldson says. "There is something about the Vineyard that makes you feel light and at ease."

And in her own family, Goldson can now watch the next generation of Black women rest, including her niece. "They may not yet understand the history, but they already understand that this is a place where they can exhale." For Goldson, that may be the simplest way to explain what Black women have found here for generations. "You can be extraordinary without having to prove your extraordinaryness," she says. "You can simply be."

Yasmine Jameelah is a seasoned wellness journalist, editor, and community builder, and the founder of Transparent Black Girl, a groundbreaking wellness platform that has reached over five million Black women worldwide. Her insightful work and leadership have been featured in The New York Times, Essence, Popsugar, Coveteur, and Oprah Daily.