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.
22 comments
No, I’ve always known about it and I would like to experience the Vinyard, not to say I’ve been but, to see what the hype is all about. I too, struggle with Black elitism and the exclusivity of it all. It’s not because I wasn’t a part of it but, because of the division that also comes with the option to practice solidarity when it’s convenient and the reality of the “proximity” to whiteness hits. When the elites are reminded of who they are and then take to express the disingenuous of black unity. That’s been my experience with the Black elite. It does righteously deserve its place in black history but, it’s not mine to be proud of, but it is one of human nature and I understand it.
I’ve been once and like you I grew up in the hood and see both sides of the coin. But it represents Black Joy and Black Excellence to me. Our ancestors and elders carved a space exclusively for them out the mud as a summer refuge. It brings me joy to know they had a happy and peaceful place to go with their families in a society that wasn’t built for them to enjoy. If it has to be expensive to preserve that nostalgia, then so be it. It’s worth every dime. Everyone will have something special to save for and visit one day. I will be back for the lobster rolls alone. I ate one every day I was there and almost broke the bank lol.
Yes, I’ve been to the Vineyard over 25 years ago. Beautiful is the only word I have to describe my experience there. Shamefully I wasn’t aware of the history at the time. Knowing the history now, raises the level of Beautiful to Eligence and, yes I most definitely have to go back.
My family has been “summering” (a word we don’t use) on the Vineyard for over 85 years. I would like to say, that we love the Vineyard and it’s rich history of the Wampanoag Indians who are native to the island Noepe, which means “land amid the waters” and the African Americans who have been on the island since the mid/late 1800’s as enslaved people (not the boujee people)and servants and then later in the whaling industry. You really should learn the history of the island before you start judging it. First, and foremost, the island’s african american community grew as a result of the Methodist summer camps/retreats, along with the islands reputation for racial inclusion helped attract black families seeking both work and a summer retreat.
I resent your comment of generational wealth on the Vineyard. Yes, our families may have purchased homes generations ago and felt that the home(s) should be passed down generation after generation. Homes were purchased as they are today, through hard work and financial planning. It’s acheivable by anyone. We are not boujee or privileged. It was/is the folks that come to visit for their weekly stay on the island that brings that mentality. Changing the name from the “Inkwell” to the “Pinkwell” honoring the AKA’s. You bring the elite socializing, the elaborate parties, the separatism. We had pure fun, and felt very fortunate that our fore parents thought and planned and saw a vision to purchase and to raise us on the island.
The island is nothing what it used to be. At least during the month of August. I purposely leave the island to rent my house out for an astronomical price, why??? because I can get a ridiculous weekly rate of $10k for my house. Keep coming back every year, and I will continue to raise the rates, because I know you will pay it.
It’s people like you that criticize our island. Please don’t criticize our island (not yours)! You’re ruining the true meaning and beauty of our island. We are trying to keep it intact. If you don’t like it…don’t come back!
Oh, by the way…very few blacks owned a “Gingerbread House” and those that did back in the 1900’s were asked to relocate their homes to outside of the “Campgrounds” Please get the history correct.
Thanks so much for sharing this incredible milestone with us! You are absolutely amazing! Doing your thing and taking up space! Your magic is simply divine!
I see experiences like this as a reminder of the capacity of success we all have. I am proud of you for making it to this level. It is beautiful and I look forward to my own induction.
I think it’s ok that this beautiful experience is cherished and valued. I also think it’s ok if it means something different to everyone either on the inside or out. I suppose it boils down to choice. Either way, it is definitely a magnificent piece of prosperous history. 🥰
I have to say though, for me this is ELITE and welcome on my end.
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