For many Black vacationers, August on Martha’s Vineyard feels like a family reunion. This year, that family included Michelle Obama, Justice Ketanji Brown Jackson, and a host of artists, politicians, and celebrities who converged for the Martha’s Vineyard African American Film Festival and a slate of cultural events across Oak Bluffs.
Earlier this month, Obama joined her brother, Craig Robinson, for a live taping of their podcast IMO, describing it as a “kitchen table” conversation. With actress Natasha Rothwell—whom they jokingly called “cousin”—the siblings traded stories about relationships, mental health, and the value of storytelling in Black communities. The warmth spilled into the audience, which cheered when Robinson playfully offered to set Rothwell up on a date.
Across town the same day, Justice Jackson discussed her memoir Lovely One, tracing her family’s journey from enslavement to her rise to the Supreme Court. Reflecting on her career, she quipped, “Where I am now, I’m pretty much stuck. So I’m glad I got it all done.”
The Vineyard, long a haven for Black travelers dating back to segregation, has in recent years blossomed into a hub for high-profile cultural festivals. The African American Film Festival, launched in 2002, now runs alongside events like the Martha’s Vineyard Comedy Fest and the newly minted Black Book Festival.
This year’s film lineup featured Spike Lee’s Highest 2 Lowest with Denzel Washington and the second installment of HBO Max’s documentary Seen & Heard, followed by a panel with executive producer Issa Rae. At another screening, Tracee Ellis Ross delighted a packed theater with her self-deprecating travel film Solo Traveling, drawing laughter from both the actress and the audience.
The week also highlighted Ralph Lauren’s collaboration with Spelman and Morehouse Colleges, celebrated through a documentary on Oak Bluffs as a beacon of Black tradition. Panelists, including Valerie Jarrett and Morehouse professor David Wall Rice, described the community as “one of a kind.”
Capping the festivities, the Rev. Al Sharpton joined Representatives Ayanna Pressley and Jasmine Crockett for a conversation about joy, politics, and activism. “The arts were the ones that financed the movement,” Sharpton reminded attendees, urging them to remain engaged.
On Martha’s Vineyard, that spirit of family, history, and resilience was unmistakable.
