What Happens on the Vineyard Doesn’t Stay on the Vineyard

Throughout the summer, your social media feed has likely given you a narrow glimpse of Martha’s Vineyard: endless all-white-attire parties, a who’s who of Black political figures and influencers, and brands unafraid to be seen with us in public despite the great DEI purge.

There was former President Barack Obama waving to onlookers during a round of golf at Farm Neck Golf Club, and Michelle Obama hitting the dance floor at Nomans. Chef JJ Johnson ran his Nightcap pop-up at the Edgartown Diner. A Great Day at Inkwell Sunrise Portrait. The Rev. Howard-John Wesley preached at the historic Union Chapel in Oak Bluffs, and Bishop Jamal Bryant brought a dose of fiery liberation theology to The Tabernacle. Artists and big thinkers cycled through the Martha’s Vineyard African American Film Festival and the Martha’s Vineyard Black Book Festival. The viral moments abound — but they still don’t capture the fullness of what the Vineyard offers America in these turbulent times.

“I see Martha’s Vineyard as a portal,” said Tiffany Lauren Jones, cultural futurist and CEO of Satori Agency, at the ColorHaus Presents: Culture Is the Inheritance event. “Every August, I feel spiritually revived, and I feel safe enough to share stories with my community here that then inspire ideas and collaborations, and to really reinvent the future of what we see coming next.”

The “Black and Bougie” caricature flattens the Vineyard into a punchline — champagne, linen, celebrity sightings — when the island has functioned as a site of Black political organizing and infrastructure-building since Reconstruction. Beyond the star-studded fundraisers, what’s happening on the Vineyard isn’t just fodder for viral moments or fuel for the 2026 election cycle — it’s laying a foundation for the decades after, with glimmers of radical imagination.

“What gives me hope is the fear that I’m sensing in our community,” said NAACP President Derrick Johnson. “Fear either paralyzes or propels.”

The myth isn’t wrong that Black excellence congregates on the Vineyard — it’s wrong about what that congregation has historically produced, and continues to produce, to power us well into the future.

A Longer History Than Your Feed Shows

Long before the Obama-era “Vineyard as Black political retreat” narrative took hold, Black intellectuals like W.E.B. Du Bois worked and relaxed here, Adam Clayton Powell Jr. cut deals and shaped strategy away from the D.C. and New York press, and the Rev. Martin Luther King Jr. frequently visited the island each summer for rest and refuge from the civil rights movement.

“If you take a look at the arc of history in America, the idea that you would have this period of what feels like almost a renaissance, followed by such severe and hostile and violent attempts to suppress it, is not so positive,” said Gillian White, chief revenue officer of Capital B News. “The thing that has happened again and again and again is that when that backlash happens, we find a way to come together. We find a way to push through, and we find a way to come out on the other side to a new renaissance.”

The Black community in Oak Bluffs traces its origins to freed and free Black families who founded the community during Reconstruction, making it one of the first Black-owned resort communities in the country — where land ownership was both a political act and an act of leisure. Shearer Cottage, the Vineyard’s first Black-owned inn, became a waystation for Black professionals, creatives, and politicians denied lodging elsewhere. The Inkwell, meanwhile, reclaims a segregation-era slur as a gathering place of pride.

“The Vineyard itself is about being able to be in a space where Black folks are able to be free — not just freedom to, but freedom from oppression,” said Ja’Bree Harris, Senior Director of Campaigns and Organizing at Color of Change. “Love kind of makes the struggle worth it. We don’t love the struggle, but love makes it sustainable.”

“We can’t go backwards. I don’t want anybody talking to me about the John Lewis [Voting Rights Advancement] Act — that’s a flawed piece of legislation. What is the real piece of legislation to protect all our rights to participate?” Johnson said. “I don’t want to talk about restoring the Department of Education. How do we create a delivery of education that’s more reflective of our young people’s needs and interests, looking into the future, not based on a model created in 1920? The inflection point now is November, and the groups here represent what is necessary — not through scarcity and competition, but through coordination and execution.”

What Happens in the Water

From porch parties to plated dinners to event activations, everywhere I turned the island was buzzing with people seeking respite, inspiration, and connection.

One of the most reliable places on the island to find all three is Inkwell Beach at 7:30 a.m., among the Polar Bears.

So many of us have taken that early morning stroll to the Inkwell, tipping slowly into the chest-high, chilly water to become a Polar Bear. Open to all, the rite of passage — celebrating its 80th anniversary this year — represents the promise of Black civic life as a rudder even in the uncharted waters of modern times.

“As Polar Bears, we say that we laugh and joke in the water, but we are serious about creating a community that knows and honors its history and acknowledges our deceased Polar Bears, our ancestors, and that we are on the Indigenous land of the Wampanoag Tribe,” said Caroline Hunter, a current member of the Polar Bears group on Martha’s Vineyard. “We acknowledge elected officials and poll workers and thank them for their service, and we encourage them to run for office, vote, and register others to vote. We talk about our community members detained by ICE. We do not shy away from the current world and the opportunity to make a difference in it.”

Part water aerobics, part prayer circle, part revival, the ritual leaves me thinking, by the time I leave the water, of my maternal grandmother’s call to action: Pray with your hands and pray with your feet.

“Given Martha’s Vineyard’s long and well-documented history of civic action, World of Hyatt saw the Polar Bears’ 80th anniversary as an opportunity to honor an organization that has made community, wellness and connection central to island life for generations,” said TJ Abrams, vice president of global partnerships and wellbeing at World of Hyatt. “Supporting the anniversary reflects Hyatt’s belief in showing up for the people, traditions and local institutions that make a destination special.”

World of Hyatt’s cocktail reception honoring the Polar Bears’ 80th anniversary during the Martha’s Vineyard African American Film Festival was a nod to two celebrated institutions founded generations apart.

Throughline Beyond 2026

Still, visitors and inhabitants on the Vineyard alike are not under any illusions. Black leaders who spoke to The Root are clear-eyed about the existential threat to our jobs, health, public safety, and Black history.

“We built this country. We were here 200 years prior to the founding of this nation, and every iteration around this experiment called democracy — almost 90% of it — is a result of us pushing the notion of who the ‘we’ and ‘we the people’ really are,” Johnson said during the Civic Leadership panel, moderated by The Root Publisher Ashley Allison. “They’re running out of white people, and that’s why you see such angst. … They want to create an apartheid reality in the United States, and they’re trying to figure out how to do it.”

To blunt this threat, Black leaders are focused on building field and communications infrastructure — candidate pipelines, donor networks, HBCU partnerships, and media strategies powered by Black storytelling — to be leveraged before, during, and after election cycles. It’s a direct answer to a common critique of the progressive movement that organizers raised repeatedly with The Root: that investment shows up too late and leaves too soon.

“I’m hard-pressed to identify $50 million spent in the Black community to turn out the Black vote,” Johnson said, calling the political consulting industry a failed business model and citing the $2 billion raised by presidential candidates during the 2023-2024 election cycle, according to FEC reporting.

“It’s a real money problem, and there has to be a sustained solution, because we know we get these campaigns built up,” said Stephanie Brown James, co-founder of Collective PAC. “The infrastructure needs to be in place in our communities year-round to support candidates, because elections are year-round — every single year, in every community.”

Brown James also pushed back on the assumption that Black people with high net worth are insulated, by proximity to Wall Street, from policies decided by people who don’t reflect, respect, or represent them.

“It’s not just about a midterm or presidential election, but the long-term sustainability of creating trusted messengers who are closest to the community, to talk about what the impact is,” said Daria Dawson of America Votes, “whether it is dog catchers, school board, city, or county, up to the president of the United States. All of us as American citizens have a voice through our vote, and we have to tap into that all the time.”

“For us, infrastructure looks like doing the work in the community,” said Aida Morrow of Social Change Fund United. “We’re a smaller, community-focused, athlete-led nonprofit, but it’s very important for us to educate the folks who are going out and voting. Infrastructure is also supporting the people who are in leadership. Infrastructure is having their back.”

A fierce urgency ran through every gathering on the island.

“Hope is this room for me, but also hope is this room not taking this conversation and filing it away, but moving into action,” Morrow said. “Progress is not perfection. Let’s just start moving.”

The Instructions

The political organizing on Martha’s Vineyard isn’t disconnected from independent Black media doing the same kind of long-horizon institution-building. At the inaugural “Beyond Medicine” healthcare equity summit, in conversation with Daniel Dawes, founding dean of the School of Global Health at Meharry Medical College, Rep. Terri Sewell, D-Ala., told the audience: “We may be facing some of the same challenges our foremothers and forefathers faced, but we’re coming at it from a totally different place.”

This moment for Black political organizers on the Vineyard is exciting, unnerving, and anxiety-inducing all at once — but the alternative is worse.

Recounting a moment with former U.S. Attorney General Eric Holder and Amelia Boynton Robinson at the 50th anniversary of the Selma march, Sewell said: “Everyone said the same thing: ‘Oh, Miss Amelia, we stand on your shoulders. We stand on your shoulders.’ When Attorney General Eric Holder got there … he sat down and he was like, ‘Miss Amelia, I stand on your…’ And she looked up and she said, ‘Get off my shoulders, all of y’all. Do your own work.’”

Boynton, a pioneering civil rights leader who helped lead the 1965 Selma-to-Montgomery marches, survived the brutal police attack on Bloody Sunday, became the first Black woman to run for Congress in Alabama, and helped secure passage of the landmark Voting Rights Act. Civil rights was her life’s work. What is yours?

That’s the Vineyard’s real inheritance. Not the view. The instructions — and they don’t come with a deadline of November, or 2028, or 2040. Whoever’s reading this is included.