Made it to Martha's Vineyard

Still no car magnet, though

In the ‘90s, I attended a private all-girls high school on a full scholarship. My classmates — along with the boys at our brother school — didn’t want for much materially. We wore uniforms of white Oxford shirts and plaid skirts or navy-blue slacks. That meant that, aside from the jewelry or loafers, you didn’t necessarily know who was wealthy or who wasn’t.

But a fair assumption was that most were doing just fine.

The school parking lot was lousy with Jeep Wranglers with oval magnets on the bumpers that mysteriously read MV or ACK. The girls’ ears glittered with diamond studs or dark blue sapphires to match their dress-code compliant slacks.

Meanwhile, I was living with my single mom in a state-subsidized apartment. These were the blessedly simple years before social media, just at the advent of the Internet. Nobody knew my situation unless I told them.

I liked to think that my boxy pre-owned Plymouth Sundance could pass for a Volkswagen Jetta, that my mall jewelry could pass as generational heirlooms. (That was probably not the case, but no one told me otherwise. I don’t think they cared.)

We’d hang out with the lacrosse players from our brother school. They seemed to be members of some secret society that required its members to wear dirty white baseball caps, Birkenstocks, and beat-up sweatshirts with the profile of a black lab on them. My blonde boyfriend and his two older brothers were part of this club, but I never directly asked what any it meant.

I had a fuzzy sense of Martha’s Vineyard as a place where rich kids and their families summered. This might have been where all my friends had their family photos shot: moms and dads and siblings in matching jeans and white button-downs, laughing along the dunes.

These were the years when New England “Americana style” had a death-grip on the nation. The Gap and Ralph Lauren and Tommy Hilfiger’s preppy ensembles were held up on a red, white and blue pedestal.

Thirty years later, I finally made it to Martha’s Vineyard with my husband and our handsome dog. Stuffed into our shiny black SUV was my denim Gap button down and navy-blue L.L. Bean quarter-zip pullover. My jewelry is real, my sense of self, assured. These days, I’m grateful to not worry about the price of a cocktail or a nice dinner out. Want that Lilly Pulitzer dress? Go for it. (But, also, do you?)

Logan enjoys summering on the Vineyard.

As an adult, I can see that none of this is out of reach. You can come to Martha’s Vineyard — or to Nantucket or East Hampton or Block Island. There are trust-fund kids and the up-and-comers, Islanders and seasonal workers. The American Dream that Ralph and Tommy were selling was always more of a dream than anything. Anyone can pop their collar and enjoy the sunset over a New England beach.

To the 15-year-old me who felt just a bit out of place with the Gap-model kids of her youth, I say, “Welcome, honey. You made it. Oh, and that black dog is just a branded sweatshirt from a mediocre restaurant.”

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Take this Trip

Start by avoiding 30 years of feeling like an outsider and just drive to the Wood’s Hole ferry in Cape Cod to Vineyard Haven, MV. Treat yourself to a can of Narraganset lager, an iconic New England brew since the 1890s, and a cup of clam chowder aboard the boat.

After you dock, stop into the Black Dog Tavern and shop (where all those kids got their sweatshirts) overlooking Vineyard Haven Harbor. I got a serviceable order of massive P.E.I. mussels in garlic and white wine.

Visit Détente for an excellent chef-driven dinner served on white tablecloths with friendly staff.

The bar at The Covington is Brooklyn-y cute.

Bad Martha is a brewery, but the pizza is what you should come here for.

Behind the Bookstore’s bakery offers a small but mighty selection of French pastries.

On Edgartown Harbor is The Seafood Shanty for lobster dip, lobster rolls, steamed lobster, and, to be fair, plenty of other seafood (and non-seafood) options.