The Hamptons has been synonymous with summer since the Long Island Rail Road first reached the South Fork in the 1870s, when New York’s wealthiest families began building vacation cottages along the dunes of Southampton and East Hampton. Artists followed a few decades later, and by the mid-20th century, the potato fields of Springs had quietly become ground zero for Abstract Expressionism, with Jackson Pollock and Lee Krasner working a few miles from where financiers now summer.
That mix has never really gone away, and neither has the crowd. Nearly a century and a half after the first grand houses went up, New Yorkers still flock to the Hamptons every June for the start of summer. Increasingly, though, it doesn’t empty back out after Labor Day. Restaurants that once shuttered for the season are staying open into the winter, hotels are extending their calendars, and a place built on summer has slowly become a place people visit and live nearly year-round.
From Southampton to Montauk is a span of roughly 30 to 35 miles, but despite its relatively small size, getting from one town to another can take quite a while, particularly during the summer—traffic simply crawls. For those posting up in the stretch from East Hampton through Montauk, this is the territory worth knowing well. A couple of picks sit farther afield, including a French bistro in a Southampton hotel and a lake house-style resort across the bay on Shelter Island, worth the extra half-hour, or on the way back to the city. Here’s where to stay, where to eat and what’s worth knowing long past the summer season.
An Insider’s Guide to an East Hampton Weekend
Where to Stay
207 Main Street, East Hampton, NY 11937
When LDV Hospitality (the group best known for Scarpetta) took over a 150-year-old Greek Revival landmark on James Lane, longtime regulars had reason to be wary, but the instinct proved unnecessary. LDV kept the whitewash and the green awnings intact and simply made the interior feel like somewhere worth lingering: Frette linens, Santa Maria Novella soap, spaghetti alla Nerano on the menu in place of the usual red sauce. The location does some of the work on its own with Main Beach, and the best of village shopping and dining are both a short walk away. It remains a top answer for anyone asking where to stay in East Hampton village.
Maidstone.
LDV Hospitality
435 East Lake Drive, Montauk, NY 11954
LDV has now set up a second act forty minutes east. Barlume Beach is a 19-room hotel on seven waterfront acres overlooking Montauk Harbor, with its own marina, a beach club and a restaurant, Barlume, that extends the Mediterranean concept LDV already runs downtown in Flatiron. The bar sets up for DJ sets on Friday and Saturday nights, running from 9 p.m. to 2 a.m., which tells you everything about what kind of hotel this is trying to be—and spoiler alert, it’s not a quiet one. Book a surf lesson through Local Legend Surf Co. before noon, while the harbor is still calm enough to pretend you know what you’re doing.
Barlume.
LDV Hospitality
81 Shore Road, Shelter Island Heights, NY 11964
The Pridwin has been standing proud on its hill above Shelter Island’s Crescent Beach since 1927, but was largely forgotten about until Cape Resorts took over a few years ago, making the case for renovating a property carefully instead of gutting it. Thirty-three rooms, 16 cottages, a pool that finally got heated and transformed with saltwater and a piano in the restaurant that gets played most nights. Manhattan cocktail institution Dante runs a summer residency here, meaning a genuinely serious Negroni is available about 40 feet from the sand. It’s a five-minute ferry from either fork, which somehow makes it feel farther away than it is, in the best way possible.
The Pridwin.
Cape Resorts
Where to Eat
29 Main Street, Sag Harbor, NY 11963
Michael Nolan grew up in Sag Harbor, left, built Fresno into an East Hampton institution, and this spring, finally opened something on the Main Street he was raised on. Miracle sits in the old Vin Sur Vingt space next to Sen, and his partner, Helen Gifford, designed it to feel like an English pub that wandered onto the water, with dark walls, low candlelight and leather banquettes you sink into. Chef Jesus Gonzalez, who also runs the kitchen at Fresno, is doing a menu of updated American classics that doesn’t try too hard to prove anything. Local tip: go for the striped bass.
Miracle.
Madison Fender
203 Bridgehampton-Sag Harbor Turnpike, Bridgehampton, NY 11932
The Roundtree Hotel owner, Sylvia Wong, ate 21 meals in a row at a resort in Bali last year and then came home having hired the chef. That’s the origin story of Nourish, and it shows in chef Dewa Wijaya’s menu, which layers Balinese instincts over classic French training, built entirely around East End produce and Montauk seafood. Takuma Watanabe, who built the bar program at Gramercy’s Martiny’s into one of the best in the country, is running drinks here, which is a serious flex for a restaurant that opened earlier this spring. Be sure to ask for a seat in the garden if the weather is on your side.
Nourish.
Judy Pak
32 Star Island Road, Montauk, NY 11954
Cucina Alba’s debut on the East End sits right on the water at Montauk Yacht Club, and the menu leans into that setting with coastal Italian built around the day’s catch, a raw bar, and a wine list that skews light and easy to drink through a long lunch. It has the loose, Aperol-in-hand energy of a proper marina restaurant, which makes sense given the boats docked a few feet from the tables. Go for sunset if you can get the timing right to take in the changing light over the water.
Alba.
Montauk Yacht Club
51 Division Street, Sag Harbor, NY 11963
Babe’s has the feel of a place that’s been on Division Street forever, though it’s only been open since this spring: eight or 14 counter seats, depending on who’s counting, tucked into what used to be Nikki’s Not Dog Stand. Julian Cavin and his wife, Martine Langatta, run it with Jonny Shipes and Arielle Shapiro; the two couples live on the East End full-time, which you can feel in how unfussy the place is. There’s no standing dinner series, despite what you may have read; instead, they bring in a rotating cast of guest chefs for one-off nights, so check Instagram before you plan around anything specific. The line forms early—plan accordingly.
Babe’s.
Babe’s
281 County Road 39A, Southampton, NY 11968
Fresh off a buzzy SoHo run, Maison Close opened its Southampton outpost this June inside The Capri, bringing the same French bistro instincts and cabaret-adjacent energy east and filtering it through a coastal lens. It’s shared plates, celebratory, and the kind of dinner that turns into a longer night without much effort. The Capri itself has leaned into that same Riviera sensibility, with $1.5 million in recent renovations (and more planned this season), pushing the property toward a St. Tropez-meets-St. Barths feel. It has given Southampton village a new hot spot you can plan an entire evening around.
Maison Close.
Maison Close
65 Tuthill Road, Montauk, NY 11954
Duryea’s has been a Montauk fixture for 80 years, and that’s because they still do what they do best: fresh local seafood in a genuinely nautical setting, water views from nearly every seat. The infamous lobster salad (currently priced at $97) is the reason people keep coming back, though the lobster roll has its own following. Most dishes are served family-style for two or three, so come with people willing to share. Get there early. By midday, the line for a waterside table stretches well past the market next door.
Duryea’s.
Carl Timpone
Where to Grab a Cup of Joe
Ralph’s Coffee, Mulford Farm Residency
10 James Lane, East Hampton, NY 11937
Ralph’s is trading its usual pop-up format for something more rooted this year: a summer residency at Mulford Farm, the East Hampton Historical Society’s restored 17th-century farmstead on James Lane, where Ralph Lauren has been a longtime supporter of the preservation work. The green truck sets up alongside white wicker chairs, green-and-white umbrellas, and lawn games through September, serving the expected Ralph’s Roast and espresso alongside a few seasonal additions, including an espresso tonic, a matcha lemonade and a sparkling pomegranate limeade called the Mulford Farm Spritz, with proceeds going to the Historical Society. Amber Waves Farm supplies the pastry case.
Last year’s Ralph Lauren event at Mulford Farm.
Hannah Turner Harts/BFA.com
136 Main Street, Amagansett, NY 11930
John and Kelly Piccinnini, the couple behind The Clam Bar and, more recently, The Corner in Sag Harbor, opened Sett Coffee at the entrance of Amagansett village this past fall. It’s a small, blue-and-white space with a geometric feature wall that photographs well, but the draw is the drink menu. Highlights include a butterfly pea latte that comes out naturally blue, a lavender latte and a matcha that’s become the shop’s default order. Pastries rotate daily, pretzel croissants especially. It’s already settled into the rhythm of the village.
Sett Coffee.
Sett Coffee
What to Do
90 Main Street, Sag Harbor, NY 11963
Sag Harbor Cinema looks like a movie theater from the marquee, but that just might be the least interesting thing about it. The 1930s Art Deco building was rebuilt after a 2016 fire nearly took it down entirely, and what reopened is closer to a small museum that happens to screen films, with art exhibitions in the common spaces, author talks and panel discussions alongside the regular schedule and repertory programming that runs well beyond first-run releases. This summer’s theme is film noir. Upstairs, The Green Bar has the best sunset in town and trivia one night a week, exactly the kind of low-key option worth knowing about.
Sag Harbor Cinema.
Sag Harbor Cinema
LongHouse Reserve, East Hampton
133 Hands Creek Road, East Hampton, NY 11937
LongHouse is easy to drive past and hard to explain until you’ve actually walked it: sixteen acres of gardens designed by textile artist Jack Lenor Larsen, built around his own house and populated with a sculpture collection that includes work by Yoko Ono, Willem de Kooning and Buckminster Fuller. It reads less like a museum than someone’s very good, very strange backyard, open to the public. The gardens themselves are open through the season, and well worth the detour on a quiet afternoon.
LongHouse Reserve, East Hampton.
Alex Marcano/BFA.com
Montauk Point Lighthouse
2000 Montauk Highway, Montauk, NY 11954
Anyone spending a summer out east eventually makes the drive to Montauk Point, and most visitors settle for a photo of the lighthouse from the parking lot before turning back. That’s a mistake. Down on the water side, the Crow’s Nest team (after reportedly trying to win the lease for three years running) just opened Lighthouse Café in the old Lighthouse Grill space. The menu is low-key, French-coastal-meets-surf-shack: croque monsieur, a good quiche, a few Basque pintxos, eaten at a picnic table with the Atlantic doing all the work as scenery. The lighthouse itself was commissioned by George Washington, the first built in New York and the fourth-oldest still operating in the country.
Montauk Lighthouse.
Laura Peruchi/Unsplash
139 Sagg Road, Sagaponack, NY 11962
Wölffer in Sagaponack is no secret, and it doesn’t need to be one to earn a place on this list. It’s the kind of destination that’s easy to take for granted precisely because it’s been there all along. Friday evenings are the move, when the Wine Stand hosts live music and the hillside turns into a very good excuse not to head home yet. Order the rosé (the original) and stay outside until the light changes over the vines.
Wolffer Main Estate.
Mark Weinberg
50 South Fairview Avenue, Montauk, NY 11954
Golf out here usually means Maidstone or The Bridge, both of which are private clubs. This is the summer that didn’t matter as much as usual: Shinnecock Hills hosted the U.S. Open in June for the sixth time since 1896, putting Southampton at the center of the golf world. The good news for everyone without a member’s badge is that the East End’s public courses are genuinely good on their own terms. Montauk Downs, a Robert Trent Jones design routinely ranked among the best public courses in the country, is the one worth planning a morning around.
