Black A-Listers Show Up and Out at Martha’s Vineyard’s Oak Bluffs, the Exclusive Hot Spot for Black Americans

Oak Bluffs has been a key center for African American culture and leisure for over a century, with origins tracing back to the era of segregation.

If you’ve been wondering where all of your favorite Black celebrities have been all summer, look no further than Martha’s Vineyard, a picturesque island just seven miles off the coast of Massachusetts. Although it’s only 96 square miles, there are plenty of restaurants, shopping and activities, particularly in Oak Bluffs, a town on the island that has a rich African American history that makes it a destination for Black people every summer. It even inspired a new clothing collection from Ralph Lauren.

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From the star-packed panel discussions to fabulous parties to quiet sunsets with family, we’re checking out all of the ways Black people are enjoying Martha’s Vineyard this summer.

A Beautiful View

@samanthacassandra_

if black joy was a place… it would be MV 🤍 #oakbluffs #marthasvineyard

♬ original sound – ℳ

One of the best things about the Vineyard is the beautiful view of the Atlantic Ocean, providing the perfect backdrop for summer vacation photos and videos.

“If Black joy was a place…it would be MV,” @samanthacassandra_ captioned her post on TikTok.

Gingerbread Houses

Besides the beautiful ocean views, Oak Bluffs has plenty of interesting architecture, like these colorful gingerbread cottages that are over 150 years old. TikTok user Abraxas gives us a walking tour.

Mara Brock Akil

(Photo by Arturo Holmes/Getty Images)

Writer-producer Mara Brock Akil speaks to the audience at the When We All Vote Reception during the African American Film Festival.

Parties With Plenty of Star Power

Photo courtesy of the subject

Dr. Jasper Brewster and singer Ronnie DeVoe of BBD and New Edition.

Michelle Obama

(Photo by Arturo Holmes/Getty Images)

The former First Lady sat down for an episode of her “IMO with Michelle Obama & Craig Robinson” podcast during the Martha’s Vineyard African American Film Festival. They were joined by actress Natasha Rothwell, known for her roles in “Insecure” and “The White Lotus,” where they discussed the actress’ career and how Obama enjoys being back on the Vineyard, calling it a “special place for us” where they “enjoy being us.”

Issa Rae

(Photo by Arturo Holmes/Getty Images)

Issa Rae looks gorgeous in green spotted out at a screening of HBO Max’s “Seen & Heard Part 2” during the African American Film Festival.

Time to Dance

@eringoldson

Networking on Martha’s Vineyard looks like Black Joy ✨ #MarthasVineyard #OakBluffs

♬ original sound – eringoldson

One thing about Black people, we can handle our business and make time to enjoy ourselves. Don’t be surprised if you find yourself in the middle of an electric slide at a networking event!

“Networking on Martha’s Vineyard looks like Black Joy,” TikTok user @eringoldston captioned her post.

Rev. Al Sharpton and Rep. Jasmine Crockett

(Photo by Arturo Holmes/Getty Images)

MSNBC host Rev. Al Sharpton and Rep. Jasmine Crockett arrive at The Color of Conversation panel discussion during the African American Film Festival.

Jennifer Hudson

Singer-actress-talk show host Jennifer Hudson dropped a beautiful photo dump on X, which included gorgeous pics from her time in Martha’s Vineyard.

Rep. Ayana Pressley

(Photo by Arturo Holmes/Getty Images)

Rep. Ayanna Pressley strikes a pose at The Color of Conversation event.

Bishop T.D. Jakes and Rev. Al Sharpton

@say.what.now97

Edgartown, Martha’s Vineyard didn’t just serve up ocean views—it brought powerful connections. 🙏 Surprised my friend and brother, Bishop T.D. Jakes, at The TD Jakes Group Global Exchange and shared a moment with Rev. Al Sharpton. Two legends, one historic setting, and endless inspiration. 🌟 A reminder that faith, leadership, and purpose can change the world. 🌊🏝 #TDJakesGlobalExchange #MarthasVineyardVibes #FaithAndLeadership #AlSharpton

♬ original sound – Say What Now

Bishop T.D. Jakes and Rev. Al Sharpton greet each other before an event on the island.

You Never Know Who You’ll Run Into

Image credit: Dr. Jasper Brewster

Spend any amount of time on Martha’s Vineyard and you’re sure to spot a celebrity. Malik Yoba posed for a photo with Dr. Jasper Brewster during his time on the island.

Staying Fit

@bossingmotherhood

How to stay active in Martha’s Vineyard and feel like you’re on vacation 🏝️ Every August, Inkwell Beach in Oak Bluffs comes alive with the Polar Bear Plunge at 7:30am, followed by sunrise yoga at 8am led by the amazing Christopher!! (Not Shawn) 🥴 Whether you’re marathon training, on a wellness journey, or just looking for a unique way to start your day — this is the recovery combo you didn’t know you needed. Bring water shoes (the rocks are no joke) and be ready to be fully submerged. Then stretch it all out as the sun rises over the water. #MarthasVineyard #InkwellBeach #MarthasVineyard2025 #OakBluffs #runner #recovery #activelifestyle #polarbearplunge

♬ original sound – Kaylyn D Stone

Folks come to Martha’s Vineyard for vacation, but many who visit also make time to stay active. From water aerobics in the ocean to yoga on the beach, TikToker @bossingmotherhood showed off some of the ways she gets in a workout in her happy place.

Bethann Hardison

(Photo by Arturo Holmes/Getty Images)

Model and activist Bethann Hardison arrives at The Color of Conversation.

Tracee Ellis Ross

(Photo by Arturo Holmes/Getty Images)

Actress Tracee Ellis Ross at a screening her of popular new series, “Solo Traveling with Tracee Ellis Ross” at the African American Film Festival.

Sharing a Sunset

@camiladechalus

There are so many amazing events going on the island right now, and I immediately felt the need to attend all of them. But being on the vineyard has forced me to slow down and enjoy the fact that this is my first summer since becoming a mom and it’s one of my son’s first times experiencing the vineyard. I’m realizing it’s these small moments that I am beginning to really enjoy the most 💕

♬ SUMMER – THE CARTERS

TikToker @camiladechalus posted a beautiful clip of her enjoying a sunset with her young son during his first trip to the Vineyard.

“I’m realizing it’s these small moments that I am beginning to really enjoy the most,” she captioned her post.  

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