I Visited Martha's Vineyard for the First Time. Let's Talk About It

Illustration for article titled I Visited Martha's Vineyard for the First Time. Let's Talk About It
Photo: Panama Jackson

Because of reality television shows and the music and entertainment scene in Atlanta, I warn everybody who is going there for the first time. As a first timer, you might think that a gate attendant will hand you a stack of singles so you can toss them at the strippers waiting for you at baggage claim at the world’s busiest and most lit airport, Hartsfield-Jackson Atlanta International Airport. You may also expect to run into a “housewife” or two or need to dodge a flying drink on your way to the party that happens as soon as you walk outside into the muggy Georgia air.


Unfortunately, the entertainment and the shenanigans aren’t just waiting for you as soon as you touch down (unless you know the right folks); you have to actually go out and find it. Atlanta, as it turns out, is a city like many others, with parks and restaurants and, well, is actually a pretty chill and regular ole nice city, where folks like Gucci Mane, Bobby Brown and Nene Leakes live.

That’s an imperfect parallel to my impressions of Martha’s Vineyard before going. Based on what I knew (admittedly very little) of Martha’s Vineyard, I half expected to get there and see a slew of older AKAs scoffing at me, telling me that I don’t even go there while sipping their mint juleps. Or that all of the black men I saw would be walking around with tennis rackets and New Balance sneakers while talking about their business portfolios. Granted, I didn’t truly expect it, but my expectations were borne out of the limited information I’d received over time about the spot. And when the Obamas began going as our first family, and after some controversy about a nonsensical quote from some MV elite’s view, oddly, on Michelle, in particular, the idea of a bougie negro hotbed wasn’t a long shot.

So imagine my pseudo-surprise when we get there and find out that MV is a place like many others; quaint, family-friendly, enjoyable and fun without nearly as much pretense as I’d led myself to believe while being expensive enough to make that upper crust, bougieness make sense.

My first introduction to Martha’s Vineyard, the frequent summer vacation spot off the coast of Cape Cod in Massachusetts, was the 1994 movie, The Inkwell, a nod to the iconic beach and its place in the history of African Americans in Oak Bluffs, though the movie itself was filmed in Swansboro, N.C.

Likely due to my location in the South, in Huntsville, Ala., and maybe because my family wasn’t comprised of alleged “bougie negroes,” Martha’s Vineyard and Oak Bluffs, in particular, were so far off of the radar that they might as well not exist. When I was in college, I read Lawrence Otis Graham’s book, Our Kind of People, which exposed me to an entire world of elite black life that I knew almost nothing about, including Martha’s Vineyard.

Sure I was at Morehouse College, one of our black “elites” institutions, but I was the first one in my family there, so hearing classmates talk about family vacations in these black enclaves was foreign to me. There are a few family members who are Greek, but I can only think of one who ever actually graduated. And Jack and Jill? I was today years old when I found out that Huntsville, Ala., had a chapter. It just wasn’t my world and the few folks I knew who did vacation up there could fit nicely into the stereotypical archetype of who visits, even if they’re all the kind of folks I hang out with regularly.


So after some early conversations at the beginning of the year, a few of my boys from Morehouse and our families made the arrangements and found ourselves in a rented house on Pequot Avenue in Oak Bluffs, Mass., for a week, seeing how the other half lives. And let me tell you, it’s pretty good.

People sit on porches all day and head to the beach and hit Circuit Avenue for ice cream and Nancy’s and eat lobster and hit up Back Door Donuts on evenings. It was an easy, breezy time. While we weren’t privy to, nor invited to, what had to be various bougie-ass negro events and kickbacks that absolutely exist, for us, it was a trip to a place we’d all heard about from friends who vacation there or live there.


I will say that it felt different, even if I’m not entirely sure what was different than heading to, say, Sag Harbor, N.Y. The African-American history in Oak Bluffs alone is fascinating and worth exploring, so being a part of a very historic enclave of blackness, especially upper-crust blackness, in America was interesting. From the moment we got off the ferry, Oak Bluffs felt so quaint and nice; the entire area is picturesque. But again, we did things we could do anywhere else: went out to eat, ate more ice cream than recommended, went to the beach and hung out with the homies.

Because we were in Oak Bluffs, we saw a huge amount of black folks though the bougieness wasn’t apparent. We were all there vacationing and running into each other and kids were living their best summer lives hanging with their friends. It easily could be the backdrop to a movie about a teenage summer love.


And it’s also expensive as the fuck; maybe that’s also what sets it apart. Just getting there is a journey and a half. There aren’t a slew of hotels on the island, so many folks rent houses for a week or however long they’ll be there, and well, that’s going to run your pockets. It ran ours. So perhaps that’s part of it—the exclusivity. You’re not just hitting up a hotel room and going to Martha’s Vineyard. Folks who own houses, many with names, rent them out during the summer months but maintain their community during the rest of the year.

I expected to get there and see exclusivity at my doorstep, assuming that the very social circles and societies I’d read about would be ever present as they got to hide in plain in sight, so to speak. I’m glad that wasn’t the case; my vacation felt just like that, a vacation. I have no idea who was up there of importance or what I wasn’t invited to. I know for a certain class of black folks, Oak Bluffs is an upper crust getaway. For my folks, it was a chance to check out some portion of black life largely absent from most of our upbringings. In the end, we were all standing in line at 10:30 p.m. on Wednesday night trying to get one of those apple fritters from Back Door Donuts.


And I hope to do it again.

Panama Jackson is the Senior Editor of Very Smart Brothas. He's pretty fly for a light guy. You can find him at your mama's mama's house drinking all her brown liquors.