Michelle Obama and Ketanji Brown Jackson Draw Crowds on Martha’s Vineyard

Black vacationers on Martha’s Vineyard often describe visiting the island in August as a kind of family reunion. If your family happens to include Michelle Obama, that is.

“This is a special place for us, because, as you all know, this is where we come to enjoy being us,” Ms. Obama said Saturday afternoon at the Martha’s Vineyard African American Film Festival, where she joined her older brother, Craig Robinson, for a live recording of their podcast, “IMO,” which she likened to a kitchen table.

The brother-sister duo were speaking with the actress Natasha Rothwell, whom they repeatedly referred to as “cousin,” inside the Martha’s Vineyard Performing Arts Center in Oak Bluffs, Mass., where many of the film festival’s events were held.

Together, they discussed mental health, dating, relationships and the importance of telling stories that reflect the Black experience. In a display of almost familial warmth, Mr. Robinson even offered to set Ms. Rothwell up with a potential suitor, which drew applause and laughter from the audience.

“Oh, God is good!” Ms. Rothwell exclaimed. “I would love to be set up.”

The quaint island off the coast of Massachusetts has been a central destination for Black vacationers for more than a century, specifically the town of Oak Bluffs, which became a popular summer destination by welcoming Black Americans during segregation when most beaches and resorts turned them away.

But with the introduction of the film festival by Stephanie and Floyd Rance in 2002, the Martha’s Vineyard Comedy Fest by Steve Capers in 2010, and the Black Book Festival by Traci Wilkes Smith in 2024, plus a busy calendar of additional events, Black politicians, filmmakers, artists, writers, celebrities and fans now converge on the island during the first two weeks of August.

Earlier on Saturday, across town, at the Island Inn, the Supreme Court Justice Ketanji Brown Jackson discussed her 2024 memoir, “Lovely One,” with Ms. Wilkes Smith.

Justice Jackson’s memoir charts her family’s journey from enslavement in the South to her grandparents’ move to Florida; her own childhood there; early stints in journalism and theater; her marriage to her college boyfriend, Patrick Jackson; and her law career, which led her to the Supreme Court.

Justice Jackson told the audience — with a chuckle — that she was grateful that she held roles as a law clerk, public defender and judge because, “Where I am now, I’m pretty much stuck. So I’m glad I got it all done.”

The gatherings this year began even before touchdown at the island’s only airport. Two women dressed in the colors of Alpha Kappa Alpha, a historically Black sorority, spotted each other as they were boarding the plane and struck up a conversation. Within minutes, they realized they had attended the same university and had mutual friends.

Buzz at the film festival, which ran Aug. 1-9, centered on films like “Highest 2 Lowest,” directed by Spike Lee and starring Denzel Washington, as well as “Seen & Heard 2” a documentary from HBO Max, highlighting the evolution of Black representation in TV, that was followed by a discussion moderated by Issa Rae.

At many events, there was a sense of lightness, conviviality and letting down your hair — a sentiment echoed by many of the festivalgoers and speakers. They spoke of how, on the island, Black people could trip and fall, laugh at themselves, and feel as though they were surrounded by family.

That was true at a screening of “Solo Traveling With Tracee Ellis Ross,” where the actress laughed loudly at her own antics onscreen, at one point covering her eyes during a scene in which her luggage was searched in Paris and security found, as she put it, “a lovely little bag that has things that are usually in your bedside table.”