Don't crucify me! I love wealthy Black folk too. We deserve to be wealthy TOO!
But this was a constant thought on my first trip to the Vineyard.
Growing up on the South Side of Chicago, the only Martha I knew was Stewart — and she had a homemaking empire. I didn’t meet “Martha’s Vineyard” until much later, somewhere in the throes of entrepreneurship and fundraising, when people started casually dropping, “Oh, we’re summering on the Vineyard.”
Summering? The only summering I knew was sitting on the porch with a cold drink, praying for a breeze.
For those who haven’t heard of it, Martha’s Vineyard is an island off the coast of Massachusetts — a summer haven for the wealthy. It’s famous for its beaches, lighthouses, and expensive-as-all-get-out real estate. But it’s also steeped in a unique and proud Black history.
A Slice of Black History on the Vineyard
Martha’s Vineyard was one of the first places in the U.S. where Black people could own property.
Over a hundred years ago, Oak Bluffs became a refuge for African Americans looking for leisure, dignity, and community — a place where they could simply exist without constant fear or hostility.
Many of the homeowners were servants and "the help" to the White homeowners in Martha's Vineyards. They needed quarters, so they built their own miniature cottages.
Black people painted them beautiful colors as an act of resistance.
Houses here can go for $1M+ and still not be “luxury” by most standards.
Yet generations of Black families have kept them, passing them down as symbols of both wealth and survival.
There’s even the “Inkwell” beach — born from segregation-era racism, but transformed into a place of Black joy, pride, and connection. They called it "Inkwell" because it was the beach Black folks were allowed to visit.
What I Loved
I’ll be honest — I didn’t even know “old money” Black folks existed until I learned about the Vineyard. Seeing a community of Black people with generational wealth was… fascinating an beautiful. It challenged my perspective of what’s possible for us.
The Polar Bear Plunge is pure magic. The Polar Bears welcome people from all walks of life to join them at Inkwell Beach every day at 7:30 a.m. from Fourth of July to Labor Day, rain or shine, except for thunder and/or lightning. The Polar Bears swim and do water aerobics in the beautiful waters of the Nantucket Sound for an hour.
People were warm, kind, and welcoming. I ran into so many CurlMixers (y’all really be everywhere), plus a ton of my entrepreneur friends. And I’d be lying if I said it didn’t feel good to be recognized and celebrated there — to feel the impact of what we’re building together.
When I went, I made sure to pack my Luscious Lotus Jelly to beat the humid air.
I also had my Ultra Hold gel handy too.
What I Struggle With
“Hate” might be too strong a word, but let’s just say I wrestle with the idea of Black elitism. Visiting the Vineyard is not cheap — you can easily spend $10K to $20K for a family of four in a week.
So naturally, a girl from my background had never even heard of Martha’s Vineyard in its hundred-year history. Spaces like this, while important, can unintentionally mirror the same exclusivity that has historically kept us out of other elite spaces. And let’s be real — that exclusivity often comes dressed in proximity to whiteness, wrapped in the bow of capitalism.
Y’all know me — I’m a social justice warrior. I can’t help but think about the people who will never be able to afford to go. Growing up in the hood makes me see both sides of the coin.
My Verdict
I’ve been once. I’d go back. But I’m not deriving my joy from saying — in my bougiest of voices — “Oh yes, we summered on the Vineyard.” I think these spaces are worth preserving and experiencing, but they’re not the only spaces that matter.
Because joy, like wealth, should be something we pass down to all of us.
So tell me — have you been to Martha’s Vineyard? Did it feel like Black elitism or Black joy to you?
P.S. They have the BEST LOBSTER ROLLS! That's undeniable.
24 comments
I have been to Martha’s Vineyard twice, the first time with friends before it became a “place to go.” We stayed at a historical cottage in Oak Bluffs that is now closed and not yet remodeled. We learned the history of Black life on the island through our host (a then-descendant of the original family who owned the cottage – a conversion of the former residence). We took an incredible tour conducted by Thomas Dresser, an author of a book on African-Americans in Martha’s Vineyard, and a friend of our host at the cottage. This visit came about because one day a group of us decided it would be nice to see certain historically Black vacation sites.
The next visit was many years later to attend an alumni event in Vineyard Haven. I, along with a few others shared a house rented by a mutual friend in Oak Bluffs, not far from Inkwell Beach. The people in the neighborhood were friendly, sitting on their porches, saying “hi” to all, and willingly engaging in conversation. The shops were quaint, and the other locations from Edgartown to Vineyard Haven equally welcoming. I learned about the Aquinnah tribe on the island and visited the Aquinnah Cliffs. I did not participate in the Polar Bears, because the ocean is very cold, but I plan to try do so on my next visit. I understand the Polar Bear group is supportive of first timers dealing with the coldness of the ocean.
Maintaining history and creating generational wealth are very important. I am so grateful that many of the Black inhabitants of MV did not sell their properties but passed them down through generations, providing us with historical insight, places to stay, and bringing forth the realization that Black wealth is achievable. MV is affordable, particularly if a group rents a house or shares space with friends.
Thank you for that thoughtful perspective. I haven’t been yet, but my daughter went this past spring with a group of friends. I believe her sorority sisters and close friends were invited by another friend maybe 4 or so of them. They had a lovely time, watching the sunset, toasting to friendship and exploring the island. I thought what a great experience to be invited and included into new experiences. My daughter suggested we should plan a trip there as well 🤣 we shall see. I have spent a decent coin on Caribbean trips for all of us so this isn’t out of reach. For me, I am good if my children are able to experience things that I may not, and I have always tried to make a way for them to have experiences that are memorable. Now that they are adults I am blessed to feel included because they always try to extend their hands to bring me along.
Vineyard life is nice been there and the joy we shared being there sparked us all to know the story and tell the story so future generations can know and believe that though we have faced challenges in the past, presently and the future… we still crise above adversity and can live life abundantly in joy never forgetting from where we and our ancestors may have come.
Yes, my family has been to the island and we were familiar with the history which is why we went. We chose to tack it on as a day trip while visiting Boston. It was a nice day and we would visit again…maybe spend a night or two. I agree that staying on the island is expensive and maybe not a possibility for some. That is the sad part. I think of us as having black joy when we are able to enjoy places like Martha’s Vineyard especially when it was one of the few places our ancestors could enjoy and relax.
Yes ma’am I was there Aug 2-9, 2025, for the MVAAFF as well as to have a good time. This was my 4th trip over my lifetime. Heard about it years ago as I studied the Kennedy Family and the surrounding area, plus a lot of my fellow Howard alumni vacation there. However, I agree with you to some extent; I determined that everything isn’t for everybody. There are just some places in this word that I won’t even be able to go based on class. However just knowing this place exist and there are Black affluent people is awesome within itself. I’m not one of those that call it “my happy place” but I do enjoy being there and understand. I’ll go back again if and when I can.
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