Do not be fooled by the Instagram tastemakers touting Montauk and the Hamptons at large as solely summer-appropriate. The Hamptons can be a really great time—all year long. All you need is a little gentle guidance. Wondering how to spend a few days out East in the off-season? Well, whether you prefer to head all the way east or to spend a weekend on the western tip of the East End, you can wonder no longer. We have you covered.
Personally, I’m a fan of starting east and working my way west, but I have always been a sucker for a fishing town in the dead of winter. If you can stomach the Friday night drive out to The End, take advantage of Gurney’s low-season prices. Included in the price of your finely appointed room? An irreplaceable view of the ocean. Cocktails at Scarpetta Beach are a must, as are a trip to the Montauk Salt Cave, where, for under $50, you can spend an hour purifying mind and body.
If Montauk feels lonely once the crowds have departed, you can always find a bustling scene at Harvest on Fort Pond, which, with its front row seats at—you guessed it—Fort Pond, feels improbably romantic in winter. Bundle up and take a hike near the Montauk Light House to the Seal Walk, where, especially in the colder months, you can see 15 to 20 local seals, sunning themselves on the rocks. In case you were worried that the bar scene had slowed with the season, you should know that the Dive of the Century, Liar’s Saloon, stays open 365 days of the year. It’s cash-only, and the bar itself is small, but you can find great solace in the affordable pitchers of domestic beer and the foosball table.
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Don’t feel like heading all the way to Montauk? No problem. The Baker House 1650 is as darling as darling gets, and it’s right in the heart of East Hampton. The 17th century bed and breakfast offers modern amenities, like whirlpool baths and flat screen televisions, but you’ll probably find yourself spending most of your time in the restaurant, eating a gut-busting breakfast (or, alternately, at the jealousy-inducing spa). Being in East Hampton offers numerous dining options, from Cittanuova for lunch to the excellent Highway Bar & Restaurant for dinner (reservations are recommended). During the day, take a drive to Sag Harbor’s Elizabeth A. Morton National Wildlife Refuge, where you’ll see a host of native birds, as well as other winter-active wildlife. The refuge abuts the beach, a slip of near-perfect sand on Noyac Bay that is worth a visit, even in the dead of winter. Better yet, hit the Refuge on a Sunday afternoon, on your way back home, and pop in to the Bell & Anchor afterwards, where, on Sunday nights, the restaurant serves one-dollar Montauk Pearl oysters. Some gluttony is required, though reservations are not.
If you’re intent on exploring the western Hamptons, consider a night or two at Water Mill’s White Fences Inn, a charming bed and breakfast within throwing distance from Duckwalk Vineyards (feel free to stop in for a taste while you’re here). Spend an afternoon walking around Southampton Village, making sure to pay a visit to the Southampton Arts Center, where rotating exhibits regularly feature the work of local artists. Agawam Park and the nearby pond, where ducks and geese take leisurely walks along the road, are worth the walk, even in the coldest months of the year. To warm up afterwards, pop into the Southampton Publick House for a pint. You can skip the food without regret, but don’t skip the rich, warming (and proprietary) Imperial Stout. For a fun throwback lunch, however, stop into Sip & Soda, where this old school luncheonette slings delicious burgers and cherry-lime rickeys. Ice cream, served in metal custard cups, is all made in house—and can be purchased by the pint or quart. For dinner, Tutto il Giorno offers compelling Italian food in a cozy setting. Of course, given the proximity to White Fences, you won’t want to skip a trip to the Parrish Art Museum, a gorgeous, comprehensive homage to modern art located right in Water Mill.