The discreet charms of the classic, East Coast–elite-style summer vacation: Devin Friedman finds his inner WASP on Martha’s Vineyard.

By Devin Friedman
June 21, 2014
Martha's Vineyard
Credit: iStockphoto

People are always going on vacation and putting on a straw sombrero and drinking a beer and feeling relaxed and saying, You know what, this is the real me. But that’s not the real you. The real you isn’t the person who is totally stress-free and good-humored and loves to make funny rum cocktails for people he barely knows, who thinks that version of herself embroiled in the careerist rat race is an impostor, who says If I just never came home and instead opened a bookstore/beach bar/sundress emporium here and bought a character-building chapeau I could spend the rest of my days being the real me. Somewhere deep inside the folds of our cortexes, we know that (1) we’re never going to move here and buy the hat and the bookstore and that (2) if we did, the old us would come and take the ferry over and hunt us down by the smell of our fear and aftershave and climb back into our bodies again and make us anxious and ambitious and money-conscious just the way we always were. Getting to not be you for two weeks is what it’s all about anyway. One of the great unsung joys of going on vacation is that you get to be a poseur. So my feeling is, pose like crazy, enjoy it, then hide the pictures of you in the hat.

Now, what kind of poseur you’re going to be is governed by what the fantasy of your vacation is. Maybe you’re going to spend a week in fingerless gloves acting like a Parisian bohemian, or like someone perpetually with a surfboard and a wet suit half-peeled off, or like a Tuscan vintner or a Russian oligarch who buys bottles of champagne for Eastern European women with tiny cigarettes. Those are all worthy poses to strike; I’ve tried them myself. But my vibe lately is the vacationing WASP. First because I personally have kind of an attraction/repulsion WASP fetish, having grown up as a hippie, broke-ish, Marxist, mongrel Jew in a preppy little town filled with blond families I resented but secretly wanted to be adopted by. But also because they have this amazing way of vacationing. Very laid-back, very chino-y, very slumming it, but with great drinks served early on the most prime real estate in the world. Beachy but not string bikini, drunk but not with Red Bull, the type of vacationing done by people with family compounds that are proudly like aging summer camps. If the ethos of the WASP vacation could be summed up by something you could hold in your fist, it would be: the lobster roll. It puts on no airs. Except that it’s, you know, lobster.

In my humble opinion, the optimal place to go full WASP for two weeks is Martha’s Vineyard. Sure, there are other East Coast preppy places. But Maine is too in-actual-fact rustic and remote. Nantucket is too for-real Waspy, which is interesting, anthropologically, but poses some problems for people who are freaked out by men who wear red pants without a hint of irony. East Hampton has come to embody forces passionately opposed by the WASP (canary yellow Lambos; Jason Binn). But Martha’s Vineyard is beautiful, rustic, understated, and Waspy without being closed and clubby. And while each town on the island embodies its own subtle take on the WASP vacation mentality, I prefer the fantasy to be had in the area known as “up-Island.” Up-Island is opposite, geographically and mentally, from the busy towns of Oak Bluffs and Edgartown. Up-Island comprises the towns of Aquinnah, West Tisbury, and Chilmark, including the village of Menemsha. I mean, it’s all right there in those names. It says: put on a bucket hat and some white stuff on your nose, drive an old beater that belies your wealth, and head over to Squibnocket beach for a bracing swim in the surf before retiring home again for a pitcher of Madrases. (If you don’t know, a Madras is a drink favored by wealthy people with boats but no feelings and is made with vodka and orange juice, with cranberry juice floated on top.) It’s all grazing pastures and stone walls and unmarked dirt roads leading to “key beaches” (your rental house has to come with a key or you can’t go). The homes you see from the road are handsome and certainly pricey but modest in their way (just don’t look on real estate websites at the aerial photos of the houses you can’t see from the road; they’ll make you think, Oh, yes, there is extreme wealth going on here, only they’re hiding it).

What’s really incredible, though, is the combination of insanely desirable real estate and obscenely low population density. Up-Island Martha’s Vineyard is perhaps the most breathtaking canvas for that New England Calvinistic austerity—just leave the land beautiful. When you think about the monstrous market forces saying BUILD A HOTEL OR AT LEAST A HOUSE WITH A HELIPAD, you are faced with another quality of New England old money: restraint.

And, along with wide, desolate beaches, imperturbably temperate weather, actual fishermen you can say hi to and act like you’re friends with while they sell you swordfish they literally just took off the boat (try Larsen’s, in Menemsha), it’s that restraint that gives up-Island Martha’s Vineyard its WASP magic. You will notice that restraint in the special register of quiet that pervades the island. The quiet of no Maseratis, of no obnoxious men buying $300 Burgundy at the Beach Plum (best restaurant on the island—no liquor license). The quiet not just of windswept dunes nestled by heather and kettle ponds surrounded by scrub pine, but the quiet of good manners. As you drive up-Island, past Tea Lane Farm or the road leading to Black Point Beach, you can almost hear the quiet of being raised right (you know who complains loudly at restaurants? The nouveaux riches) hissing from your tires.

A corollary of that Calvinistic simplicity: there’s this little hippie commune thing going on up-Island. You can see it at the West Tisbury Farmers’ Market, where fresh-faced college students who spent the summer pulling turnips are working the stands. There’s a whole back-to-the-land vibe at the Tea Lane Farm and the Mermaid Farm Dairy (the most insane feta cheese you will ever taste, made from the milk of cows grazing on the most valuable grasslands in the world) and the farm and flower stands. You can hardly drive up-Island without passing an unattended honor-system farm stand (take what you like and leave money) of the kind that hardly exists anywhere else now.

I suppose there are people who come here and live among the weathered shingles and farm fields and believe they’re keeping it real. But that’s not what’s going on. Up-Island Martha’s Vineyard is no more real than the Paris section of Las Vegas, except that the structures are actually old and reflect a culture that once was. It is a kingdom under glass. That’s what’s fascinating about Martha’s Vineyard: it is both real and fake. A facsimile of something that is also the authentic version.

But the best thing about Martha’s Vineyard is that it’s by far the most accepting place to be a WASP poseur. It’s historically the place all kinds of non-WASPs come to pretend to be WASPs: black people famously like to vacation here, and Jews, and presidents, and nouveaux riches who don’t want to act like jackasses. So there’s that. You don’t have to worry about being  found out. You can just enjoy the quietude and lobster rolls and quahog chowder and arguing over who can acquiesce and give the right of way more quickly and happily when two cars meet each other on one of those dirt tracks. I don’t care if I’m not really one of them. As long as I get a parking space at the beach I’m pretty happy.