The Best Things to Do in the Hamptons During Winter

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Just because it’s not 80 degrees doesn’t mean there aren’t plenty of things to do in the Hamptons.

While the Hamptons sees its biggest surge of visitors in the summer months, the East End—lauded for its long stretches of white-sand beaches and celebrity residents—has an abundance of draws in the colder season, too. Traffic is more manageable, hotel prices are more affordable, and those hard-to-get reservations are a bit easier to snag. But without the opportunity to take advantage of the area's famed beaches (though they’re still there for the brave), one may ask: are there even things to do in the Hamptons, sans beach time? The answer is a resounding yes, which makes this a cozy and creative weekend destination for those looking for a quick getaway from New York City. These are the best things to do in the Hamptons with the arrival of chilly weather.

Curl up by the fire at The Maidstone Hotel

The Maidstone 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 year-round. Feel free to grab one of the many coffee table books situated around the property and curl up near one of the fireplaces. As for their restaurant, there may be no better time to dine on their Swedish-American fare than in the winter months. Hearty dishes like the köttbullar (Swedish meatballs) are the cold-weather favorites, and nothing will warm you quite like a slice of their freshly baked pies. 207 Main St., East Hampton; 631-324-5006.

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Tour the Montauk Lighthouse

For a modest $12 admission fee (adults), you can tour the oldest lighthouse in New York State. 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. While open during the colder months, the hours change seasonally, so be sure to check the website before planning a visit. 2000 Montauk Highway, Montauk, NY 11954; 631-668-2544.

Luxuriate at The Inn at Windmill Lane

There’s no need to ever leave your room at The Inn at Windmill Lane, which offers three different types of stays, each with a very private feeling: seven suites in the main house (opt for suite 1, a duplex with a huge soaking tub and double shower); 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). 23 Windmill Ln., Amagansett; 631-267-8500.

Courtesy Inn at Windmill Lane

Taste the cozy reds at Wölffer Estate

Wine connoisseurs and novices alike will enjoy the experiences offered at Wölffer Estate, an American winery in the classic European tradition. Although renowned for their summer rosé, the vineyard also offers an enticing collection of red wines, ideal for cooler months. Visitors can also take part in Candle Light Fridays, held from 5 p.m. - 8 p.m., which includes live music; wines are sold by the glass or bottle and paired with cheese and charcuterie. Of all the things to do in the Hamptons on Saturday afternoon, relaxing at Wölffer is one of the most popular choices, so go early to snag a table or call ahead to book a tour of the property.139 Sagg Rd., Sagaponack; 631-537-5106.

Shuck and sample at Widow’s Hole Oyster Farm

Shellfish aficionados know that when it comes to eating oysters, colder months are your best bet. “Oysters taste best in the winter,” says Mike Osinski, owner of Widow’s Hole Oyster Farm. Visitors to the village of Greenpoint, located on the North Fork (a short train or car commute from the Hamptons) can get a tour of the farm, see how the oysters are grown, visit the nursery and learn how to shuck oysters. Most importantly, you get to sample them. 307 Flint St., Greenpoint; 631-477-3442.

Get in the holiday spirit at Gingerbread University

If you’re traveling to the Hamptons with children around the holidays, a visit to Gingerbread University is a must. Attend a one-hour decorating session, which includes a sturdy gingerbread item to decorate, and icing and candy with which to adorn your gingerbread. The ginger elves are there to help as you and your family create lasting (and sugar-filled) memories. Reservations for this architectural sugar rush are encouraged but not required. 631-727-7309; 3225 Sound Avenue, Riverhead, NY 11901.

Snag a reservation at 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 the same Mediterranean menu with ingredients from local farmers and fishermen, but visitors can actually snag a table in the off-season. And while every table may not be back to back high-rollers, don’t be surprised if you spot Alec Baldwin or another East End celebrity regular.136 N. Main St., East Hampton; 631-324-3550

Browse the Parrish Art Museum

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. Coming up from November 2019 to January 2020 is their Artists Choose Artists 2019 exhibition. Seven of the area’s noted artists select photographers, sculptors, painters, or other artists to feature. Ultimately, a total of 14 up-and-coming artists comprise this inspiring exhibition of local talent. 279 Montauk Hwy., Water Mill; 631-283-2118.

See Nancy Atlas Project perform in Amagansett

Make like the locals and catch a performance of the Nancy Atlas Project while you’re out east at Stephen Talkhouse, the Amagansett bar where Jimmy Buffett and Paul Simon have performed. Atlas opts for a medley of both original songs and covers; her performances, suitable for all age groups, tend to draw an eclectic crew that takes to the dance floor. Her audience is mainly locals and visitors who know where to find her.1 Bay Street, Sag Harbor.

Shop the high-end brands at Tenet

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—such as Intermix and Calypso—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 bi-annual scouting trips to Paris to discover brands before his competitors. 91 Main St, Southampton; 631-377-3981.

Ice-skate at 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. The “clubhouse” serves as a bonafide snackbar. Ice-skating costs $7 to $27, depending on the day and skater’s age, and skate rentals are $9 for adults.178 Buckskill Rd., East Hampton; 631-324-2243.

Wine and dine at The American Hotel

There’s always a crowd at The American Hotel, where guests can grab a table for dinner by the Steinway or purchase a cigar to stroll along Sag Harbor’s Main Street. And while there is always someone interesting hovering on the porch or in the dining room of the eight-room hotel during the summer months, such as Ralph Lauren (or someone who looks like they just stepped out of his catalog), the colder months allow more privacy in the historic space. The origination of The American Hotel dates back to the whaling era of the 1840s, so it’s worth spending some extra time within this East End staple learning about the history the stately space has seen. 45 Main St., Sag Harbor; 631-725-3535.

Sample Dopo La Spiaggia’s classic Italian

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.

Courtesy of Baron's Cove

Enjoy live music at Baron's Cove

Baron's Cove is the brainchild of Curtis Bashaw, the New Jersey hotelier whose other properties (Congress Hall, The Virginia) have turned Cape May into a go-to destination for not only families but a surprisingly chic set. And while the Sag Harbor property (renovated by Bashaw in 2015 from its original state) is the quintessential Hamptons property in the warmer months, with a view of the harbor and a pool, it has just as much to offer during the winter. Besides 67 spacious guest rooms, with living room areas and nautical touches, Bashaw's sister, Colleen, designed the bar and lounge space with a year-round feel—wintertime guests will love the wood-burning fireplace. It’s a popular spot for both visitors and locals that is crowded nightly (claim your seat early) and offers both impressive cocktail and a wine lists. Live music is performed on the weekends as well, so plan to stop by, whether or not you’re staying on the property. Have dinner beforehand at The Restaurant at Baron’s Cove, which sources ingredients from local farms and fisheries, like North Fork Egg Farm, Peconic Gold Oysters, and Mecox Bay Dairy, among others. 31 W. Water St, Sag Harbor; 844-277-6672.