If you’ve ever read Dr. Beach’s “Top Ten Beaches” list, you can understand the appeal of the Hamptons. Beautiful beaches combined with stunning landscapes and vineyards, mansions inconceivable in their extent, sitting beside traditional shingled cottages. Also, some of the best produce in the country.
The Hamptons, on the South Fork of Long Island in New York, are a group of hamlets, villages and towns lying along the Atlantic Ocean.
The area is a perpetual playground for the rich and famous and for city dwellers who appreciate a beach escape in a rural setting within a short drive of New York City.
In the off-season, as the months after autumn are known here, the Hamptons remain a popular destination. The arts come alive with plays, concerts and exhibits to fill days and evenings.
Picture-perfect towns are dressed up in their holiday finest, with houses, trees and shops donning shimmering lights and colorful garlands. Beaches take on a different cast, the icy-blue sky and ocean in vivid contrast to the white sand and dunes.
Dress warmly and you can still enjoy a peaceful walk as you admire the waves and homes along the coast.
A Dozen Choices for Dining Hamptons-Style
This is the time to visit the Hamptons’ hard-to-book restaurants that are thronged during “the season.” Additionally, you’ll avoid the notorious summer traffic.
While Friday and Saturday nights may still be a bit dicey for preferred-time reservations, you’ll find cozy spaces available on other nights, with hearty specials adding a sweet lure.
An extra attraction: the 2026 winter Long Island Restaurant Week includes several Hamptons restaurants and runs from January 25-February 1, 2026.
Almond, Bridgehampton
French bistro Almond has numerous well-priced specials during the off-season. Meatless Monday at the restaurant offers a special no-meat prix fixe selection. There is also a two-course prix fixe meat option for those who would still like to indulge.
Tuesday features burgers and beer, along with the full menu, while Wednesday offers bottomless mussels and fries. Saturday night is fun night with karaoke and DJ Lama. On Christmas Eve, the restaurant reprises its annual suckling pig roast.
Nick & Toni’s, East Hampton
A difficult reservation during the summer and fall, the celebrity fave is a cozy choice for the off-season when tables are easier to come by. Pizza is a standout, available on select days from the wood-burning oven.
Wednesday through Monday, Nick & Toni’s serves pastas and dishes made with seasonal ingredients.
For the off-season, the restaurant has revived its popular two-course prix fixe. The dining spaces and bar area are intimate, and service is friendly and kind. A lovely wine list is offered.
Sen, Sag Harbor
Off-season is the time to avoid the lines at this no-reservations Japanese gem. Solid omakase and à la carte Japanese fare prepared with the freshest ingredients available make Sen an upscale year-round favorite. Sen is perfect for dining and sake sipping before or after Bay Street Theater.
Highway, East Hampton
The popular East Hampton restaurant serves seasonally inspired comfort food. Dishes include miso-glazed salmon and spit-roasted organic chicken with sourdough stuffing and butternut squash, perfect for cold-weather dining.
For a sweet finish, the Milk Pail apple crumble is truly drool-worthy. On select Thursdays, Highway schedules its popular Asian Night.
R.Aire, Hampton Bays
Spanish Chef Alex Bujoreanu keeps things warm and cozy at R.Aire with a menu of Basque and Mediterranean dishes. Combined with local influences, the menu features paellas and tapas.
Wines by the bottle or glass and the restaurant’s own white and red sangrias are perfect cold-weather accompaniments.
A three-course prix fixe menu is featured Tuesday through Friday along with 30% discounts on select bottles of wine. Happy Hour specials include lobster rolls, oysters and discounted beverages.
Il Capuccino, Sag Harbor
An informal restaurant that many consider their hometown dining room, “Il Caps” offers red-sauce favorites like spaghetti and meatballs and chicken parmesan, along with their acclaimed clams and garlic rolls.
Chianti bottles hanging from the ceiling add to the comfortable vibe. Reservations are only taken for four or more, so walk-ins are typically easy.
Bell and Anchor, Sag Harbor
The popular Sag Harbor seafood-leaning restaurant has a weekly schedule of four special evenings during the off-season.
Tuesday night features Chicken Milanese, Wednesday is Lobster Night, Thursday brings about Bouillabaisse Night, and Sunday headlines Moules Frites.
Bell and Anchor takes a short hiatus in January.
La Goulue Sur Mer, Southampton
New to the Hamptons scene, Manhattan fave La Goulue opened its Hamptons outpost in the space formerly occupied by Enchanté and Little Red, a stylish stand-alone restaurant with warm Parisian brasserie vibes.
The room is stunning, set with red leather banquettes, candlelit tables with white tablecloths, and a central floral arrangement.
La Goulue Sur Mer’s menu is classic French, with dishes like steak frites, soupe à l’oignon, tuna tartare, and tarte tatin accompanying local oysters from Montauk and salads featuring local produce.
On Wednesdays, the restaurant offers $1 oysters and a special bistro-style burger that will perish any preference for a smashburger.
An extensive wine list includes numerous choices by the glass with selections ranging from California to France. There’s a small bar, too, if you prefer to have a sip and a snack as you enjoy the restaurant’s curated playlist.
Feniks, Southampton
The Hamptons’ newest entry into the fine dining category, the striking restaurant reconfigured the space previously occupied by long-standing restaurant Le Chef.
Now filling two levels, the sceney eatery features a chef’s counter with a tasting menu and à la carte dining focusing on Mediterranean dishes. Feniks is closed on Tuesday.
Limoncello, Southampton
Casual and conveniently located next to Southampton Playhouse, Limoncello opened this year, replacing Paul’s Italian Restaurant.
The café presents a well-priced Italian menu, and the earnest staff serves polished cocktails and generously portioned dishes including pastas, pizza and the outstanding Limoncello chicken.
Calissa, Water Mill
Whitewashed and airy, the Cyclades-style restaurant offers a menu of all-time Greek hits. Off-season, Calissa transports you to a winter après-ski setting replete with white fur throws and seats, and white lights decorating pine needle-covered counters and walls.
The evening menu celebrates the “Chalet” experience further with fondues, mulled wine and hot toddies, along with cold-weather selections like avgolemono soup, moussaka, roasted chicken marinated in a light yogurt sauce with herbs, and grilled lamb chops.
DJs spin on Friday and Saturday.
Bistro Eté, Water Mill
A year-round go-to for Hamptonites, Bistro Eté goes all out for the holidays with seasonally infused dishes and homemade desserts. Chef Arie Pavlou prides himself not only on his French culinary prowess but also on his ability to create dishes that are as beautiful as they are delicious.
His smoked pork chop is a sculptural feat, topped with a pumpkin cup with a side of winter squash puree. Seasonal flavors also appear in homemade ice cream and the creative cocktail list – try the truffle martini if it’s available.
Special menus for Hanukkah, Christmas Eve, and New Year’s Eve are offered.
Spirits to Keep You Warm
The Hamptons’ vineyards and distilleries don’t close after the fall harvest. You can enjoy a warm-spirited afternoon all winter long at these wonderful places.
Sagaponack Farm Distillery, Sagaponack
Warm up with Sagaponack Farm Distillery’s handmade distilled gin, potato vodka and rhubarb liqueur in the distillery’s tasting room open Friday, Saturday and Sunday. Light bites are available.
Wölffer Estate Vineyard, Sagaponack
Wine lovers are invited to the Tasting Room at Wölffer Estate for an afternoon of wine tasting and charcuterie featuring popular vintages like Cabernet Franc, Chardonnay and rosé.
Special winter events include Candlelight Fridays with live music and December’s Winter Wonderland celebrations of food, wine and firepits for the whole family.
Duck Walk Vineyards, Water Mill
Low-key Duck Walk continues their tastings in the off-season with well-priced flights of red, white and dessert wines. Reservations are suggested.
Inn-Type Accommodations Abound
Topping Rose House, Bridgehampton
The elegant Topping Rose House invites you to enjoy the serenity of the Hamptons off-season with a spa getaway. The Spa by SLH package offers a night in the hotel, breakfast for two and one spa treatment per person per stay.
Add dinner at Jean-Georges at Topping Rose restaurant and you’ll enjoy a perfect escape without driving.
The Baker House 1650, East Hampton
The elegant Baker House embraces the winter season with ‘Intimate Moments at Baker,’ a focus on togetherness and family. A striking bed and breakfast with architecture inspired by the 17th-century Cotswolds, the Baker House was built in 1648 and has a storied history.
Serving first as a residence for a sea captain, it later became a tavern, a meeting hall and a site for religious services before its transformation into a lodging establishment in 1996.
Baker House provides a mix of refinement and comfort with indulgent amenities, including an on-site spa. Popular during the colder months, Baker House’s heated outdoor igloo sessions are bookable for guests and non-guests to enjoy wines and snacks.
Canoe Place Inn and Cottages, Hampton Bays
On the site of America’s oldest inn, Canoe Place has been re-imagined using its original building and ballroom as focal points for a cozy stay and dining experience.
During the holidays, the inn is especially welcoming with its fireplace room, intimate Good Ground Tavern, bar and spa.
The Ram’s Head Inn, Shelter Island
The Hamptons have their own beautiful island, too. Shelter Island feels like a world away once you’re on the car ferry from Sag Harbor.
The historic 17-room Ram’s Head Inn is distinguished by its relaxed yet luxurious accommodations, dining options, lively lounge, and polished service. Fireplaces and water views keep things cozy in the off-season.
Southampton Inn, Southampton
A comfortable location for a family-oriented getaway, Southampton Inn offers the personal attention of a bed and breakfast with the services of a hotel. The 90 guest rooms each have a slightly different décor.
Claude’s restaurant is popular for its signature weekend brunch, which features locally sourced ingredients. If it’s not too chilly, you can use the inn’s bikes and helmets to ride to nearby Cooper’s Beach or around town.
Holiday Tour of the Inns
The inns of the Hamptons are dressed up in their holiday finery in the winter. East Hampton and Amagansett invite visitors to wander through a selection of the towns’ charming inns on December 13 to enjoy the decorated interiors along with seasonal refreshments.
As part of this festivity, LDV at the Maidstone proffers cider, prosecco, hot chocolate and holiday cookies. If you decide to book a room, the inn is offering a special package with a two-night minimum stay.
You’ll receive a welcome hot chocolate and a special Maidstone hat to keep you toasty as you explore the inn’s location in the historic district of East Hampton.
Shopping For Gifts and Deals
Shopping is more than a casual pastime in style-obsessed Hamptons, and the off-season entices with special prices and holiday markets.
On December 13 and 14, the By Hand Artisans Holiday Gift Show in East Hampton presents a market of gifts handmade by local artisans. You’ll find distinctive fused glass, knits and felted wool, original jewelry, wood crafts, sea glass art, skincare and soaps, mosaics, wooden toys, and ceramics in historic Ashawagh Hall.
Main Street in East Hampton and adjacent Newtown Lane are home to high-end luxury and independent designers, including Nili Lotan, Ralph Lauren and A.L.C., as well as local favorites like BookHampton, Jones Road, and Obligato.
Sag Harbor is like a Hallmark Christmas card over the holidays, with its harbor illuminated with lights and holiday decorations adorning the shops, restaurants and 18th-century homes.
On the second Saturday of every month, the village presents SAG Saturdays, an open-door celebration featuring gallery shows, author readings, live music, tastings and family-friendly activities.
Warm up with a hot chocolate or honey-cinnamon latte at Grindstone Coffee and Donuts before spending time at Sag Harbor Books with its unusual mix of rarities and bestsellers.
Southampton boasts a shopping area that’s not in a mall or located on a main thoroughfare. Jobs Lane and Main Street are pedestrian-friendly, encouraging window-shopping of the holiday-decorated pop-ups and stores that remain open during the holiday season.
Fashion specialists like BA&SH, Tenet and Dazzelle hold sales to encourage gift-giving or self-indulgence.
The Arts
LongHouse Reserve
At the 16-acre reserve and sculpture garden in East Hampton, LongHouse Illuminated: A Magical Winter Experience turns the landscape into an enchanted world after dark with glowing sculptures and light-lined garden paths.
ZIMA!, the garden’s annual theatrical adventure presented by the Neo-Political Cowgirls Dance Theater Collective, is an immersive walk through the illuminated pathways.
The Parrish Art Museum
Beautifully illuminated during the holidays, The Parrish Art Museum in Water Mill is home to galleries with rotating exhibits by local artists and works about local subjects.
This year’s exhibits include Nina Yankowitz: In the Out/Out the In through February 22, 2026, and Endless Limits: The Work of James Howell through February 8.
Southampton Arts Center (SAC)
At Southampton’s popular cultural hub, SAC, the off-season continues the program of rotating exhibitions, plays, film screenings, art workshops and holiday markets.
Second Skin, a group exhibition exploring the intersection of art and fashion, runs through the end of 2025, showcasing works by international artists and designers and positioning clothing as a powerful medium for articulating identity, expressing gender and cultural differences, and advancing political activism.
Southampton Cultural Center
A local gathering place, the SCC hosts comedy shows, theater, family-friendly activities, dance classes and art exhibits in an informal space.
Southampton Playhouse
Now including an intimate IMAX theater and three additional screens, the fully renovated Southampton Playhouse movie theater blends the latest blockbusters with discoveries from around the world, alongside eclectic repertory programs.
Guild Hall
East Hampton’s cultural center, Guild Hall serves as a museum, performing arts theater and education center. During the winter, student art exhibits, local ballet performances, comedy and HD screenings of Met Opera performances are highlighted.
Bay Street Theater
Sag Harbor’s Bay Street Theater offers winter programming with comedy shows, classes, and the ever-popular “Nancy Atlas Fireside Sessions” in January with musician Nancy Atlas and guests.
Stephen Talkhouse
Talkhouse is a small music club in Amagansett that hosts indie and current rock and folk acts throughout the year.
In addition to local favorites like Nancy Atlas and Lez Zeppelin, surprise guests Metallica, Paul McCartney, Bon Jovi and a variety of singer-songwriters have been known to perform there.
Walks and Hikes
South Fork Natural History Museum (SOFO)
SOFO’s walks, tracking sessions and astronomy nights encourage visitors of all ages to connect with local wildlife and nature. Seal cruises, birding sessions and nature walks are scheduled all year.
Hiking and Nature Parks
Many hiking trails are open during the off-season months. Parks like Mashomack Preserve on Shelter Island, Walking Dunes in Napeague, and Hither Hills in Montauk are located near beaches for added challenges and vistas.
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