Things to Do in the Hamptons During the Winter

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For a luxurious weekend road trip from New York City filled with wineries, (heated) al fresco dining, and nights spent cozied up by your suite’s private fireplace.

The Hamptons sees its biggest surge of visitors in the summer months, but from wineries to new al fresco dining options (with plenty of heat lamps and chic semi-open-air bungalows), the Hamptons in the winter make for a perfect NYC escape. Traffic from Manhattan slows considerably in the winter, but there are still just as many cold-weather things to do in the Hamptons, whether you’re after a weekend of shopping, culture, and wine, or are keen on family-friendly activities for the whole brood. We’ve gathered the best Hampton hotels for wellness seekers, culture-filled outposts for a wintery sojourn in Montauk, and of course, the best restaurants to dine-in and takeout from. Here, the Departures luxury guide to winter in the Hamptons.

The Best Hampton Hotels for a Luxe Weekend Away

Gurney's Montauk Resort & Seawater Spa

Courtesy Gurney’s Resort Montauk

Gurney's Montauk Resort & Seawater Spa is open all year around and is the only Hamptons escape set right on the water. Of the 152 rooms, suites, and beach cottages, we’d recommend a beach cottage for a winter weekend, so you can bundle up and enjoy the ocean views from your private deck, or sit by your fireplace inside. From the resort’s 2,000 feet of private beach lined with daybeds to the luxurious Seawater Spa debuting in 2021 after a reimagination from the designer of New York and Barcelona’s Aire Ancient Baths, winter in Montauk has exceptional hygge vibes at Gurney’s.

Shou Sugi Ban House

Fredrika Stjarne/Courtesy Shou Sugi Ban House

For the couple or group looking for an over-the-top wellness retreat, take to the 13-room Shou Sugi Ban House, a Japanese-inspired spa in the Hamptons. Next to the Parrish Art Museum, this revelatory property infuses Japanese meditation principles into its design (see: the signature charred wood) and healing spa treatments. The idyllic sanctuary on three coveted acres in Watermill, New York specializes in customizing personalized wellness rituals to each guest.

The Reform Club

The Reform Club has a choose-your-own-adventure take on luxury accommodations. They have seven suites in the main house; three one-bedroom cottages; and The 21 House, a four-bedroom luxury farmhouse. A former low-key inn, the property was revamped in 2009 and is the perfect getaway for those looking for a winter retreat. With double-sided fireplaces, and homey touches, like artwork from the owner’s private collection, the property feels simultaneously super-luxe and ultra comfortable. Their concierge service will make sure you don’t lift a finger while on the property: they’ll chauffeur you in their fleet of SUVs, stock your room with the gourmet groceries of your choice, and even deliver food from nearby restaurants (which they’ll plate and serve to you on linens in your preferred private dining area). 

The Maidstone Hotel

The Maidstone Hotel is quaint, with just 16 rooms and three cottages. But for those looking for a homey atmosphere in the colder months, it’s a perfect fit. The hotel prides itself on their "Scandinavian Cozy" design concept; the building itself could pass for someone's personal home, and the employees urge guests to treat the common areas like their own living room. The property is decked out in bright Josef Frank patterns, sheep hides, and an abundance of plants. Feel free to grab one of the many coffee table books situated around the property and curl up near one of the fireplaces. 

Hamptons Wineries to Visit in the Winter

Bedell Cellars, North Fork

Bedell Cellars is a family owned North Fork winery that’s stood for 40 years—it was founded by Kip and Susan Bedell in 1980. Forty years later, they’re still known for their merlots, and for winos who love a warm wintery single-varietal red, they also do a lovely cab franc and petit verdot. Bedell is open from 11 a.m. to 5 p.m. daily and seatings are first come, first serve.

Wölffer Estate Vineyard, Sagaponack

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Wine connoisseurs and novices alike will enjoy the experiences offered at Wölffer Estate, an American winery steeped in classic European traditions. Although renowned for their summer rosé, the vineyard also offers an enticing collection of red wines, ideal for cooler months. Of all the things to do in the Hamptons on Saturday afternoon, relaxing at Wölffer is one of the most popular choices, but you can book a private cellar tasting for your group of two to six people to enjoy a completely customized food and wine pairing.

Channing Daughters Winery, Bridgehampton

Blending wine and art, Channing Daughters in Bridgehampton sits on 28 acres of vines, including their Sculpture Garden Vineyard. With a plethora of white and red varietals, many aged in French, Slovenian, American, or Hungarian oak, Channing Daughters Winery also wades into the world of skin contact with orange wines. For the vermouth drinkers or cocktail lovers, they even make a line of fortified wines. Wander the property and pick up wine on the patio (or have it delivered locally for free).

Where to Eat From the North Fork to Montauk in the Winter

Bungalows by the Sea, Gurney’s Resort Montauk

Courtesy Gurney’s Resort Montauk

This winter, Gurney’s is rolling out a brand-new dining concept: Bungalows by the Sea. The al fresco dining offers private bungalow seating and fire pits from November 2020 through March 2021. The bungalows, for up to six people, must be booked in advance for $25 per adult—but 100 percent of that money goes to a local charity like East Hampton Meals on Wheels. The seasonal menu at Bungalows by the Sea will include elevated comfort food (think: oysters Rockefeller) and exceptional craft cocktails

South Edison, Montauk

One of our favorite East End hot spots, South Edison is seating at limited capacity and open for takeout. Their menu has always featured inventive takes on local seafood, seasonal favorites (their pasta in celebration of heirloom tomato season is particularly exciting), and upscale turf for the non-seafood crowd (think: Wagyu steak tartare and succulent crispy duck).

Dopo La Spiaggia, Sag Harbor and East Hampton

Dopo La Spiaggia is yet another example of how the East End of Long Island is becoming more and more like the Upper East Side. Maurizio Marfoglia, ex-partner of Gabby Karan and alum of Coco Pazzo, is a co-owner of our favorite little trattoria on Bay Street in Sag Harbor. There’s a charming outdoor garden come spring-summer, but when the Hamptons cool off, the cozy rooms inside this intimate-but-happening place will do just fine. Choose from their East Hampton or Sag Harbor locations. The Dopo La Spiaggia team has also recently opened Argento South, a charming restaurant and cocktail bar in Southampton for a more relaxed (though still quite chic) dining experience.

Nick + Toni’s, East Hampton

Eric Striffer/Courtesy Nick + Toni's 

If you’ve always dreamed of hobnobbing with the celebrity crowd at Nick + Toni’s, but have never been able to score a reservation, winter is the time to do it. The East Hampton eatery, staged to resemble a rustic farmhouse, offers a Mediterranean menu with ingredients from local farmers and fishermen, but visitors can actually snag a table in the off-season—even with limited-capacity seating. If you prefer to take out, don’t be surprised if you spot Alec Baldwin or another East End celebrity regular when picking up your food.

Things to Do in the Hamptons With Your Whole Family

Buckskill Winter Club 

For serious ice skaters, Buckskill Winter Club offers the only outdoor, NHL regulation-sized ice rink in the Hamptons. But you don’t need to be a pro to hit the ice here. Visitors of all ages can enjoy the rink, as it offers everything from public skating to private lessons, figure skating to hockey classes, and junior and adult hockey leagues for regulars. Ice-skating costs $7 to $27, depending on the day and skater’s age, and skate rentals are $9 for adults. 

Gingerbread University

Courtesy Gingerbread University 

If you’re traveling to the Hamptons with children around the holidays, a visit to Gingerbread University is a must. You can now pick up a do-it-yourself gingerbread or cookie kit for the whole family to enjoy. The gingerbread kits include sturdy gingerbread items to decorate, and icing and candy with which to adorn your gingerbread. While you can’t decorate on the premises with the ginger elves at the moment, you can instead bring the architectural sugar rush back to your rental home or hotel suite.

Montauk Lighthouse

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Through Dec. 20, you can tour the oldest lighthouse in New York state and wander the stunning Turtle Hill grounds, overlooking Turtle Cove. Constructed in 1796, Montauk Lighthouse was designated a National Historic Landmark by the Secretary of the Interior in 2012. The “keepers” of the lighthouse were members of the U.S. Lighthouse Service and the U.S. Coast Guard, until the lighthouse was automated in 1987. 

Culture-Filled Things to Do in the Hamptons All Year Around

Parrish Art Museum

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The East End may not seem like a mecca for art (especially for those coming from New York City), but the Parrish Art Museum has 12,000 square feet of exhibition space and more than 3,000 paintings, sculptures, and multi-media holdings. And it’s all set on 14 acres of sprawling Long Island meadow. Visitors must reserve tickets in advance to visit the galleries.


There is a reason many stores (and hotels and restaurants) in the area close up shop in the colder months: lack of clientele. But for those looking for deals, now is the time to get to the racks, as many of the stores on the East End slash their prices in an attempt to move inventory before the warmer weather merchandise hits stores. If you’re looking for something more unique than the usual staples, try Tenet, a favorite of Hamptons regulars located on Main Street in Southampton. Founded in 2010 by former financier Jesse Warren, Tenet carries both women’s and men’s clothing from brands like Isabel Marant, Golden Goose, Cushie et Ochs, Zimmerman, APC, Alex Mill, Our Legacy, and Gitman Vintage. Warren makes biannual scouting trips to Paris to discover brands before his competitors. 

Widow’s Hole Oyster Farm

Shellfish aficionados know that when it comes to eating oysters, colder months are your best bet. Visitors to the village of Greenpoint, located on the North Fork can get a tour of Widow’s Hole Oyster Farm to see how the oysters are grown, visit the nursery, and learn how to shuck oysters. Most importantly, you get to sample them after touring the oyster farm, which sources shellfish for some of the best seafood restaurants in Manhattan.