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. 

Get it here. 

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.