The Summercamp Hotel in Oak Bluffs, MA.
I took an airplane…all of the way to Massachusetts and a place that’s been on my list since probably 2000. That’s right. I finally landed on Martha’s Vineyard.
Right after college, I read Our Kind of People by Lawrence Otis Graham. The book documents the lifestyles of upper middle class Black families and their social clubs and organizations over the 19th and 20th centuries. This was a world mostly foreign to me — a Southern girl whose vacations were pretty much trips to Memphis and Mississippi where my family has roots.
I had a certain curiosity not only about these families, but also this vacation spot. In my mind I had built it up to this mythical status, whose legend only grew once the Obamas made it a destination, and I was aspiring to be my bougie best. I imagined streets filled with notable folks and beautiful beaches where my kind of folks rested our elegant heads.
Now, there still may be all of that somewhere and sometime, but what I saw in Oak Bluffs was a beach town, similar to others I’ve visited in the past like Biloxi, Myrtle Beach, and Destin. You have your waterside restaurants and a plethora of souvenir, ice cream, and sweet shops — most of which are lined up along one strip. In Oak Bluffs, that strip is Circuit Avenue, and I went there several times over my weekend trip. Oak Bluffs was the destination because that’s where I heard my people are, and upon arrival, the Uber driver as well as staff from the Summercamp Hotel confirmed that Oak Bluffs is where you have fun.
We were starving once we landed, so the first step after checking in was getting a late lunch. Nancy’s, which is right on the water, is a tourist trap, but it was also tasty New England chow. I felt like splurging, so I got the lobster special. Now, I don’t know how to actually eat lobster, so I ate the meat that I could see. The rest of the greenery accompanying the plate was delicious. After that, we walked the town and picked up a drank at a real live package store, which I immediately recognize as a liquor store because that’s what we still call it in the country, too.
Night one was a little chilly, but we went out to Flavors, a little spot that was “lit” — at least as lit as you can be in this era of COVID-19. I did my first group Electric Slide in over a year, and that felt good. The next morning we ate breakfast at Biscuits, a local legend, and decided to do the bike ride from Oak Bluffs to Edgartown. That’s a seven-mile scenic ride that includes the well-known Inkwell Beach and a bridge famous for being in Jaws.
Edgartown was actually my favorite place TBH and probably more of the vacation atmosphere I sought. The shops and restaurants — even the ice cream — were upgrades to what we had in Oak Bluffs. It’s here where I found a pair of silver hoops to add to my jewelry collection, and the streets were a wonderful place to explore on our bikes. Our Edgartown adventure started with a tasty lunch that included an octopus tail and a lobster watermelon salad from 19 Raw Oyster Bar. We also stopped to get some incredibly delicious ice cream from Vineyard Scoops and then rode off to see the beach and lighthouse. I loved the beachfront as well as the lighthouse. It would have been nice to bring a picnic and lay looking and listening to the ocean for the afternoon.
Back in Oak Bluffs, I wanted to arrive in time to visit the Mariposa Museum where I’d seen quilts in the window the day before. I’m on a mission to buy some art and was eager to see what they offered. While I didn’t find anything to my liking or price range, it was great to learn about the history of the shop. For an early dinner, we picked up Jamaican food from Vineyard Caribbean Cuisine and were serenaded by the local who’d given us some restaurant recommendations the day before. The later dinner was Fat Ronnie’s, where I was reassured by the staff’s T-shirts that assured us that they were all vaccinated. The bike ride zapped my energy, so there wasn’t much life to that night. I had my Zzzzzzzs.
The next day we just had the morning, and it was time for one last breakfast along with some souvenir shopping.
Now that I understand some of the lay of the land, when I return, I will:
Stay in Edgartown and stay for at least a week.
Bring along friends and family for a larger party.
Rent a hotel or AirBnB that offers complimentary bike rentals. This was one convenient perk from the Summercamp, which has a relationship with a bike shop that’s on the same block as the hotel.
Do more activities like kayaking and seeing more of the island.
Plan ahead. While reserving the airfare was pretty easy, the hotel search was intense, and many of the boutique hotels required deposits or full payment in advance.