Even if you knew nothing else about it, you would feel, driving up to the Pridwin, which occupies prime real estate on Shelter Island’s Crescent Beach, a sense of history. The waterfront hotel and restaurant has survived 91 years on the island, and has lived to tell about it.
Its architecture — floor to ceiling glass windows from a porch that faces the sunset, white clapboard — speaks to easy, breezy summer living, which, truth be told, has not changed all that much since the 1920s. Gatsby-esque aesthetic aside, this is no East Egg. And everyone here is just fine with that.
Sitting on 10 acres of land, the hotel continues to operate seasonally, much like its down-the-beach competitor, Sunset Beach. Home to a tennis court, private pool, docks, small beachfront area, bar, and restaurant, the hotel provides lodging in the form of water-facing rooms and woodland cottages. It remains popular even now, close to 100 years after it first opened. Which is to say: Good luck getting a room in season. You’ll need to book well in advance.
One event you can attend, however, even if you didn’t happen to book well in advance, is the Pridwin Wednesday Barbeque. Starting at the end of June and concluding right before the Labor Day holiday, the hotel’s restaurant hosts a weekly cookout on its lawn. For $40, diners are treated to an all-you-can-eat outdoor feast, with sprawling water views, communal picnic tables under umbrellas, beer served in plastic cups from mobile kegerators, and a lot of food. Alcohol isn’t included for the price, and diners must show their IDs to get an armband for this privilege, but beers are, generally speaking, affordable.
The cookout menu changes, of course, on a weekly basis, but the concept remains largely the same week after week: Corn, potatoes, kid-friendly buffet items, some manner of shellfish (beware; the shrimp cocktail goes fast), steaks, hot dogs, hamburgers, fresh fish, salads, and pastas all make an appearance. Diners are welcome to return as many times as they wish, although the lines — which begin right before the buffet opens, at 6 PM — are long.
For those with a penchant for a good view and less of a penchant for an elbow-your-way-through dining experience, the restaurant serves memorable food, too. Tempura-battered softshell crabs come with local squash blossoms, and Peeko oysters — from the Peconic Bay — are served with a fresh mignonette. Entrées include an obligatory (but extremely well executed) Crescent Farms duck and sausage, served with seasonal vegetables. Those in the mood for an upscale lunch can enjoy the Pridwin from 12 to 3 PM daily in season, where a lobster roll, Niçoise salad, blackened fish sandwich, and meal of buttermilk fried shrimp are served in an impeccable setting.
Still, the Wednesday cookout speaks to the spirit of the Pridwin: casual, freewheeling, lively, and imbued with the exuberance of summer. Live music plays as the sun sinks into the bay. Farther down Crescent, at Sunset Beach, you’ll have to wrangle over-coiffed millennials with overactive Instagram habits for a spot anywhere near the sunset, but at the Pridwin — a far more appealing scene, I must admit — the sprawling view is available for every diner to take in. If you end up with a table closer to the hotel, never fear. Bring your own blanket and take your hot dog and shrimp cocktail down the lawn for a memorable night on the East End.
The final cookout of 2018 is nearly upon us, so get there while you still can. The restaurant recommends calling ahead, so that it can adequately prepare for the number of guests.