Where to Eat, Sleep and Explore in the Hamptons Whether It's Summer or Winter

·21 min read

For New Yorkers, a sojourn in the the Hamptons is always a good idea. There's nothing like a beach getaway to help recharge the batteries and reset the mind, and with a post-vaccinated summer finally underway, travel is starting to feel right again.

Another reason to head to the Hamptons is because this eastern Long Island conglomerate of hamlets and sea villages is actually a weekend-worthy escape any time of year.

Related: 67+ Family Beach Vacations for 2021

Summer will always be considered peak season for the best time to visit the Hamptons, but don't discount its potential in the fall, winter and spring. There are picturesque farm stands and orchards prime for picking and kid-friendly activities in the fall, cozy refuges with fireplaces and cocktails in the winter and endless outdoor dining options and shops to peruse in the spring. Plus vineyards and wine tastings galore.

The crowds also tend to calm down after Labor Day—as do the prices—making the fall and winter seasons a smart time to go if you're trying to avoid the tourists. Regardless of when you do decide to venture Out East, we've rounded up the best things to do in the Hamptons year round. Peruse our picks then get ready to pack your bags.

How Do You Get to the Hamptons

There are numerous ways to get to the Hamptons, but if you’re concerned with social distancing, your best bet is to drive. It’s around two and a half hours from New York City and probably the cheapest way to go, aside from spending money on gas and putting miles on your car. From Connecticut, it’s two hours and from places in Massachusetts, you’re looking at five hours (or more, based on traffic). That’s just to enter the Hamptons, mind you. If you’re traveling to Montauk (the end of the line), tack on another hour or more with traffic.

The ferry is also a lovely way to go, given you get to cruise into town on a boat—with drinks and food. There are ferry routes from New London, CT to Sag Harbor and Orient Point, or Bridgeport, CT to Port Jefferson Harbor at the end of Route 112. Then, you can either drive or Uber to your end point. Get more information on ferries here.

How Far Are the Hamptons from NYC

Other ways of transport to the Hamptons from NYC include the Hampton Jitney. It’s $29+ for a bus ticket, BUT they have free WiFi and snacks. The journey via Jitney can be around 2 to 5+ hours, depending on traffic. Then, there’s the MTA Long Island Railroad. A train ticket will cost you $22+ and the trip can take anywhere from 1.5 hours (on the ‘Cannonball’ from Penn Station), to 3+ hours, depending on your stop. And yes, you can fly. Although the last option needs to be the most complicated and expensive, unless you own a private jet or want to spend $795 a seat on BLADE. East Hampton Airport and Long Island MacArthur Airport are the two closest airports for regular flyers, however.

Things to Do in the Hamptons in the Summer

The question is: What isn't there to do in the Hamptons this time of year? From lazy beach days and town-to-town shopping trips, to lobster bakes, fitness classes, outdoor music concerts and more, the Hamptons is back and better than ever.

For more information on beach permits and parking, check out this handy guide.

Break a Sweat

Grab a bike for SoulOutside at The BARN in Bridgehampton, but be sure to book early—classes fill up fast Out East.

If you'd rather bike, but not to the beat, there's always the old-school way. Most hotels provide complimentary wheels to scoot around in the summer and there are plenty of bike lanes, and picturesque towns to peruse by peddle. Should you be in a house or Airbnb, here are a few more bike rentals to try: Khanh Sports, Amagansett Beach & Bicycle and Dan’s Bike Rental.

Plan a Clambake on the Beach

For a true Hamptons-style feast, a clambake on the beach is a must. DIY'ing it yourself can be a bit time consuming however, so leave the cooking to the pros. Hampton Clambake will bring the beach party to you, with custom kitchen trailers and tools to drive onto the beach or to your home for a fully-organized clambake on the South and North Forks. Enjoy the sun and the surf, watch the sunset, crack some claws and be ready for the quintessential Hamptons experience.

Explore "The End of the World" (Montauk)

Enjoy the scenic views from the oldest lighthouse in New York State at the Montauk Point Lighthouse Museum, catch your dinner with Montauk Fishing Charters, ride the waves at Ditch Plains, give bird watching a go at Shadmoor State Park or horseback riding at Deep Hollow Ranch.

Take a Wellness Break

Ever since its opening two years ago, Shou Sugi Ban House has been the go-to wellness mecca in Hamptons land. For starters, it's breathtaking, with a massive Buddha sculpture at the entry and a living room style lobby flanked by cushy daybeds that envelop you as you sink in. From there (if you can get out of said loungers), you'll sample a plant-based lunch consisting of raw bowls or perhaps, Summer Greens Grilled in Seaweed. Then it's onto a sound bath, meditation session, lymphatic massage or their Earth and Sea Body Scrub, to slough off any lingering sand from the weekend. They also have a state-of-the-art gym and heavenly pool to cap off the full-circle healing experience.

NYC-based ORA is bringing their highly-curated and elevated acupuncture experience to the Hamptons for in-home or poolside treatments at your hotel this summer. Choose from acupuncture, cupping, gua sha and E-Stim—an ancient Chinese medicine healing experience. They'll also be popping up at Soul Cycle BARN in Bridgehampton with two custom treatment rooms all season long.

Where to Stay in the Hamptons in the Summer

EHP Resort & Marina gets our top vote in terms of overall excellence for location, value, amenities and luxe cottages and suites complete with fireplaces, kitchenettes (stocked with dishes and glassware sourced from the Amalfi Coast, mind you) and a tennis/pickleball program offering private lessons, group sessions and a doubles night on Tuesdays. Spanning nine waterfront acres in East Hampton, they have everything you could need onsite, so you never have to leave: a delicious breakfast bakery, Buongiorno, with City of Saints Coffee and lemon-filled Bombolonis, complimentary bikes and poolside yoga classes, a shuttle to take you to nearby beaches, a partnership with SLT East Hampton to squeeze in more workouts, curated music dinners at acclaimed restaurant Si Si and the most adorable bunnies parading the grounds, looking to be 'grammed. Should you be arriving to the Hamptons by boat, they even have their own Premiere 58 Slip Marina for dock-to-door ease. 20% off midweek rates and a "One More Night" promotion when you book three or more makes staying here a no brainer.

The Maidstone in East Hampton is another great pick for proximity to everything, shopping and a slew of notable restaurants. Bonus: It's adorable. Each of their 19 rooms is inspired by a different Scandinavian luminary, has quirky furnishings and fixtures and pets are welcome in most. Should you require a bit more space for family-style lodging or a girls' getaway, they also have a few roomy cottages with kitchens and patios that lead out to the main garden. Breakfast is served daily (and included in your room rate) and the on-site restaurant and bar is convenient for grabbing a bite before hitting the beach or nearby Parrish Art Museum.

Also noteworthy in Montauk: The Surf Lodge which is basically Montauk HQ all summer long for the best weekend concerts, pop-up shops and classic Hamptons vibes. TSL is also ideal for a couples trip or girlfriends' getaway, since it's a notorious summer hangout. As far as the rooms are concerned, they're laidback, but equipped with the essentials—and hammocks. You can easily walk or bike to the beach and your quarters come with Hamptons-style getaway must-haves: a mini fridge to store drinks and snacks, comfy Casper beds, free WiF and artwork by surfers.

Where to Eat in the Hamptons in the Summer

Duryea's! Dining at Duryea's is a rite of passage in the summertime. Not only is the food spectacular (see their famed Lobster Cobb Salad evidenced here), but the unparalleled ambiance warrants a drive out to Montauk alone. Tables line the dock under a canopy of fish net and the laidback energy and flowing rosé make you want to never leave.

Mediterranean-inspired Si Si is quite possibly the buzziest restaurant (re)opening this summer at EHP Resort—where everyone wants a resy. After debuting under the radar during the pandemic last year, it really feels as if this is their moment right now. The place is always packed, the pastas are incredible and the sunsets even better (with those dockside views)! The restaurant-adjacent bar also becomes a full-on scene scene to keep the party going until the wee hours, but back to those pastas... Do not pass go on the Spicy Rigatoni with Lobster or the Wild Morel Mushroom Quadrotti with Crispy Leeks and a snowfall of black summer truffles on top. And if you're feeling really hungry (or have a huge crew with you), there's a Si Si Paella for four, overflowing with spicy lamb, sausage, casteltrevano olives, sofrito and all the shellfish.

Si Si's sister restaurant Sunset Harbor is around the corner and a more chill option for lunch, happy hour oysters and a game of cornhole by the boats outside. Overlooking Three Mile Harbor, it's a chic little spot outfitted by decorative pieces from Morocco and Greece, serving all the fresh fish along the likes of Shrimp Scampi, Mussel Cazuela with Coconut Broth and Seafood Fra Diavolo. An extensive sushi and nigiri menu rounds out the list of reasons to go.

NYC hotspot Kissaki has three locations Out East in Water Mill, Kissaki Sushi in Montauk and O by Kissaki in East Hampton, which is our personal favorite for their blend of Japanese and Italian cuisine known in Japan as Itameshi. Dishes like Wagyu Caviar Crispy Rice, smoky-meets-creamy Dashi Pasta, Lobster Zeppoles and Summer Corn with Tonkatsu mayonnaise, parmesan cheese and lime are standout hits, but there's also an array of grilled steaks, salmon and tuna with your choice of sauces: Japanese Barbecue Sauce, Yuzu Zabaglione or Balsamic Teriyaki. Their also known for their futomaki rolls—like the Maguro Mama Futomaki (spicy tuna, sweet potato tempura, cucumber and
avocado)—all presented in a lovely little garden in the back.

You might be in the Hamptons, but you'll feel like you were transplanted to Uruguay after dining at Mostrador Marram—the sister restaurant of La Huella and Santa Teresita in Jose Ignacio, Uruguay. We can't wax poetic enough about this gem in Montauk. Guests of Marram are well aware of the culinary magic behind Mostrador, but for those of you who are not in the know: go for the fresh-baked breakfast pastries that are out of this world, a rustic lunch spread consisting of family-style salads plus grilled veggies, and wood-fired pizzas at dinnertime.

Montauk's newest dockside darling is La Fin Kitchen & Lounge. It's literally at "The End" of the island, but it's well worth the trek for the posh seaside restaurant vibes and French farm-to-table fare. Inspired by St. Barth's and St. Tropez's famed all-day beach clubs, they offer everything you need for a recovery brunch (with healthy vegan snacks and smoothies), or a coastal-themed dinner. Order the Cauliflower Flat Bread, Fresh Spaghetti with Lump Crabmeat and Anchovy Breadcrumbs and Whole Grilled Black Bass for two, with leeks and local potato.

Morty's Oyster Stand is another Napeague/Amagansett favorite, located smack dab in the middle of the main Montauk Hwy drag. With a rotating list of East Coast oysters and a killer Tuna Poke Tostada, it's a smart choice for a chef-driven lunch or dinner when you're tired of the same ol' spots. PS, the notorious BBCs from former tenant "Cyril's Fish House" are still on the frozen cocktail menu. That would be rum, coconut, banana, cocoa—with or without a floater.

If you happen to be near Sag Harbor, visit one of our nearest and dearest, Lulu Kitchen & Bar, for lunch or dinner. The casual (yet always packed) bistro features wood-fired cuisine along the likes of Grilled Spanish Octopus, Mussels A-La-Plancha, Grilled Heirloom Cauliflower and Khachapurri, a Georgian-style cheese-filled bread dish with egg, Raclette cheese and yogurt sauce on the side. They also have a dreamy backyard oasis for al fresco dining and a superb wine list.

You CANNOT beat Carissa's The Bakery for coffee, breakfast, cakes, gelato or fresh-out-of-the-oven croissants and baguettes. No matter where you're staying, make it a point to visit this East Hampton/Sag Harbor steadfast for seasonal specialties like their Summer Squash Reuben, Baby Zucchini with Stracciatella Salad, Omakase Berry delight and Spicy Chicken Sandwich. It's their over-the-top pretty cakes that deserve all the attention though—and pre-orders.

We love Moby's in East Hampton for its ever-changing Italian menu of wood-fired pizzas, pasta and salads, along with bottled cocktails under lantern-lit tents. Post dinner, their lawn becomes the place to be for late-night drinks and chatter around the fire pits. 

Calissa, a trendy Mykonos-esque restaurant in Water Mill, is known for local Montauk fish, Greek food, killer cocktails and an A+ summer entertainment lineup. The Mediterranean mainstay launched two different music series' this summer: Broadway Out East featuring some of the biggest stars of the stage on Thursday nights and Calissa Sounds on Fridays, which will bring performances by the likes of Wyclef Jean, Questlove and DJ Cassidy, among others.

Navy Beach is always a fun lunch spot (with the kids or without), since it's set in the sand with picnic table-style seating. It can tend to get crowded though, so we suggest making a reservation or going when they open so you can enjoy yourselves—and baskets of crispy fish and fries or the Navy Burger.

Turkish-inspired food is captivating guests out East this summer with the arrival of El Turco East Hampton. Signature dishes include: Roasted Beet Hummus, Red Lentil Balls, Ali Nazik Kebab (a smoked pureed eggplant topped with cubes of sautéed lamb) as well as a variety of fresh summer salads and other tantalizing small plates. Do not leave without getting the Manti (small beef dumplings topped with garlic yogurt, sumac and dry mint).

More restaurants we're partial to in the summer include: Almond (Bridgehampton), Fresno (East Hampton), Bell & Anchor (Sag Harbor), Beacon (Sag Harbor), Bostwick's Chowder House (East Hampton), The Backyard at Sole East (Montauk), Wölffer Kitchen (Amagansett), Le Bilboquet (Sag Harbor) and Elaia Estiatorio (Bridgehampton). When you need a lobster roll break (is that even possible?), there's Elaia for mezze platters, souvlaki and all the spreads.

Things to Do in the Hamptons in the Fall

While most onlookers consider the Hamptons to be a summer-specific destination, those in search of cooler-weather activities wait until the leaves start to change to visit this slice of Americana. Festivals and concerts are still going on in the early fall months, but there are museums, art installations and plenty of farm (plus wine) stands to explore during autumn. There's also hard cider to be sipped, apples to be picked and who doesn't love a crisp walk on the beach in a hoodie? We sure do.

Best Apple Picking & Pumpkin Picking in the Hamptons

Related: Best Apple Picking Near Me

Where to Stay in the Hamptons in the Fall

One the best year-round havens in the Hamptons can be found at Baron’s Cove, in the quaint whaling village of Sag Harbor. Ideal for a fall, winter or summer retreat, the sophisticated refuge boasts Harbor Suites with striking waterfront views and over 50 nautical-minded rooms—many with private gated patios for sunset sips. Their massive pool is a big draw for families traveling with kids and the dog-friendly policy lets you bring your furry BFF along for the trip. They even have a Travels With Charley package inspired by late author (and longtime guest) John Steinbeck and his pup Charley. Love Baron's too much to leave? Book the hotel for month-long extended stays designed for families working remotely or homeschooling, and want to trade city life for small-town charm.

The writer's loved compound is also known for their killer breakfast (order the lobster Benny!), in addition to live jazz and cocktails on the porch. Truman Capote was a regular in his heyday—always in and out for libations and inspiration—and The Restaurant at Baron's Cove has one of the most romantic dining rooms in the Hamptons, overlooking the boats.

The Roundtree is another fall favorite for a family-friendly, couples or solo getaway. There are cozy cottages and spacious suites with Frette Linens, Matouk Towels and Grown Alchemist Bath Products, an expansive lawn made for bocce and s'mores by the bonfire, plus complimentary fresh-baked cookies in the afternoon. It's also within walking distance to tons of cute shops and restaurants in town and they offer electric Beach Buggy shuttles to the beaches in the area, as well as a free beach parking pass.

Related: 33 Safe Vacations You Can Still Take During the Coronavirus Pandemic

Other reasons to stay include their pets welcome policy and an adorable Lemonade Stand kids can rent and operate, then give their earnings to the charity of their choice. 

Where to Eat in the Hamptons in the Fall

iL Buco al Mare in Amagansett is the storied brainchild of independent filmmaker and owner Donna Lennard, who enlisted longtime iL Buco Chef Justin Smillie to open their first outpost Out East. Let's just say, if you have to choose a restaurant for a special celebration, this is it. Smillie's ancient grain focaccias, imported tinned fish from the Iberian Peninsula and wood-fired fare are so so good, you'll be dreaming about everything you savored long after the last bite. And the space—incredible! With one-of-a-kind oil paintings from Italian artist Antonello Radi framing the walls and a charming patio for wine-fueled luncheons, it's the sort of special place you never want to leave.

You can't go to Montauk and not do dinner at Scarpetta at Gurney’s Montauk Resort. It's a must for a romantic date night and is known for signature dishes like Creamy Polenta with a Fricassee of Truffled Mushroom, Tuna 'Susci' and Short Rib and Bone Marrow Agnolotti. Not to mention it's one of the most beautiful restaurants in the Hamptons, located directly on the beach with indoor and outdoor dining and a top-notch wine list. 

Lobster Roll aka LUNCH is a Hamptons haunt for the best hot and cold lobster rolls, fish and chips, crab cakes and Key lime pie—since 1965. With picnic table seating in the front and a whimsical, dreamy garden in the back, the retro seafood shack is the perfect pit stop for lunch or dinner on a day trip in the South Fork and you can't beat their chowder and chili. PS, if you've ever seen The Affair, you probably recognize this famed eatery from the hit TV show.

K Pasa is a Sag Harbor must for the best breakfast and tapas year-round! Don't forget the tacos either. It's hard to choose between the Baja Fish Tacos, Blackened Salmon and Chicken Tinga Tacos with Avocado Cream, so order a sampler, plus the Impossible Chorizo Quesadillas and tots. It's right on the water and always hits the spot when you need a break from stuffy and just want delicious. Top off your order with a frozen Prickly Pear Margarita and go home happy.

Main Street Tavern revamped the old Indian Wells stomping grounds in Amagansett last summer and it's already become a neighborhood staple in no time. We can't rave enough about their simple, yet impeccably well done menu, with dishes like Tavern Wings, Baked Clams, the Steak Sandwich and more. Out back, there's a super-cute beer garden for lazy weekends spent washing down fish and chips with a couple cold ones.

And if you're making this a foodie trip, other strong contenders for breakfast, lunch and dinner in the fall include: Cowfish (Hampton Bays), Coche Comedor (Amagansett; by the team behind Nick & Toni’s), La Fondita (Amagansett) and Towline BBQ (Sagaponack).

Related: 90 Best Staycation Ideas

Things to Do in the Hamptons in the Winter

For a beachy enclave, you'd be surprised at how many homes, hotels and restaurants boast fireplaces around these parts. There's nothing like curling up with a good book, glass of wine and a blustery view of the ocean after all. When you do want to venture out, there are still viable options in the winter and we predict many more Hamptons businesses might extend their season, given the ongoing situation. Most museums are open year-round, as well as a sampling of must-try restaurants and shops. Since you won't be beach hopping, try town hopping with map-less drives the lead to the best discoveries.

Hamptons Museums to Check Out

Take a Spin Around the Ice Rink

One of our other beloved winter pastimes is ice-skating at the Southampton Ice Rink. They also offer skate school, public skating and adult hockey.

Go Off Leash at the Dog Beaches in the Hamptons

Walks on the beach are another tradition, regardless of the seasons in the Hamptons, and furry friends are allowed to roam free (off-leash) during off-season months.

Where to Stay in the Hamptons in the Winter

Gurney's Montauk Resort & Seawater Spa and Gurney's Star Island. Though Montauk is synonymous with summer, the destination is just as alluring in the winter, when the crowds disappear, holiday lights are abound and the sand is adorned with fresh snow. For the holidays, check-in to the only year-round resort in the destination, Gurney’s Montauk, which truly caters to travelers looking for a “home-away-from-home” vibe, especially during these uncertain times. The suites and cottages come aptly decorated with a Christmas Tree, trimmings, lights and festive cookies and/or a Menorah with Gelt and candles. Even better, the property will have eight beachfront bungalows complete with a seasonal menu, firepits and all the festive cheer to help celebrate the holiday season. There will also be complimentary fitness and wellness classes, interactive programming for kids (like bingo and a scavenger hunt) and a special dinner at Scarpetta to ring in the New Year.

Where to Eat in the Hamptons in the Winter

Nick & Toni's. It's completely possible to be dining next to Gwyneth Paltrow, or Hillaria and Alec Baldwin on any given night at Nick & Toni's, an old-school Italian landmark loved by celebs and locals alike. The Easy Hampton restaurant, which opened its doors in 1988, has a Tuscan farmhouse feel and is known for specialities like Whipped Ricotta & Speck Flatbread, Zucchini Fritto, Grilled Veal Chop, and Bone Marrow, Sweet Potato Cavatelli with Long Island Duck Ragû and an epic Bloody Mary menu.

Bridgehampton Inn & Restaurant is also open year-round and so charming (both the hotel and the restaurant).  The owner Sybille is a wealth of knowledge when it comes to the area and her Loaves & Fishes Food Store next is stocked with whimsical, one-of-a-kind goods you can't find anywhere else. Plus, any place that serves S’mores Creme Brûlée is Parade approved, if you ask us!

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