How to Experience Montauk and the Hamptons Like a Local

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At this point, no one would argue that the Hamptons are a scene. When New York City empties out on summer weekends, you can bet that majority of them are headed east to the towns, villages, and hamlets along the eastern end of Long Island—including Montauk, East Hampton, Southampton, Bridgehampton, Amagansett, and Sag Harbor.

If you’re not a local (or a summer loyalist), it’s easy to get stuck on trendy spots like Gurney’s that’ll empty your wallet and threaten your sense of personal space when tourism is at its peak from June through September. (P.S. Any regular will tell you the best time to visit the Hamptons is in September, when the number of visitors thins but the weather remains idyllic.)

Heading east and want a more enjoyable experience—one that’s not reminiscent of what you’d get in NYC? These local recommendations will help you beat the crowds and have a more authentic experience on eastern Long Island.

Marra Montauk Courtesy Image

Where to Stay

Not everyone can afford a pricey Hamptons summer share. And the prices per night at luxury hot spots like Bridgehampton’s Topping Rose House,  Easthampton’s The Maidstone, as well as Montauk’s Ruschmeyer’s and the Surf Lodge can be through the roof during the crowded summer months. Fortunately, there’s a slew of other hotels that are just as cool. (If you don’t have a car, get from NYC to eastern Long Island via the Hampton Jitney or the Long Island Rail Road.)

In Sag Harbor, rest your head at Baron’s Cove, a historic hangout for legendary figures like Truman Capote, Paul Newman, Art Garfunkel, Billy Joel, and Jackson Pollock. The intimate harborfront property is a short walk from Main Street in the charming hamlet, which shouldn’t be overlooked for it’s louder, buzzier neighbors.

Across the way in Bridgehampton, Room at the Beach is a former motel turned 10-room boutique hotel that opened in May. The 1.5-acre lot is shaded by towering redwood trees originally planted by one-time owner Martha Stewart (Donna Karan was also a previous owner). This iteration feels like a woodsy escape, even though it’s just a mile from the beach.

For a quieter weekend experience in Montauk, book a room at Marram, the area’s newest boutique hotel, which opened in mid-August. The oceanfront resort features cedar buildings, muted colors, and airy, open spaces that maximize the natural setting. It’s a much calmer vibe than most Hamptons hotels. There’s morning yoga, nightly bonfires, and a surf program run by nationally renowned surfers from the area.

Those craving a livelier stay can bunk down at The Montauk Beach House in the heart of downtown Montauk. The 33-room property is just a block from the ocean and a quick walk to the shops, restaurants, bars, and cafés. There’s plenty of action on site, too, with poolside music that starts at 1 p.m. and lasts through sundown.

A lobster roll, slaw, and chips from Duryea Lobster Deck in Montauk, NY
A lobster roll, slaw, and chips from Duryea Lobster Deck in Montauk, NY Courtesy Image

Where to Eat

There’s no shortage of good eats in the Hamptons, but you can lose hours waiting for a seat at the most popular spots. There’s no need to fight for seats at places like Sag Harbor’s Le Bilboquet or East Hampton’s Nick & Toni’s.

Bistre Ete is way quieter than your average East Hampton restaurant, with a French-inspired Mediterranean menu. Candy Kitchen in Bridgehampton is your classic diner experience (and every beach town needs one of those). And Round Swamp Farm, with its original location in East Hampton and a market in Bridgehampton, has the freshest produce in town and carries prepared foods for when you don’t actually want to eat out.

In Montauk, it’s all about the views. “George’s Lighthouse Cafe is home to the best sunset views,” says Joe Attanasio, co-founder of 29MONROE, a pop-up event planning company in Montauk and Manhattan. The cafe—which serves a casual seafood menu—is open from 10 a.m. through sunset, and sits right on the water at the tip of New York’s East End. “One of my family’s favorite spots for dinner is Inlet, down by the entrance to the harbor on the east side near the Montauk Airport,” says George Filopoulos, owner of Gurney’s Resorts. “They serve terrific sushi and offer equally amazing views of the sunset.”

Best Pizza & Dive Bar
Best Pizza & Dive Bar Courtesy Image

The lobster rolls at Lunch are a Hamptons classic; it’s busy, but the tables turn over quickly. And “Duryea Lobster Deck in Montauk has popped back into popularity, and is a beautiful place for lunch and dinner that’s not too hectic,” recommends Chris Heyn, a New York commercial real estate agent who summers in Sag Harbor and East Hampton. “It reminds you of being in the South of France or on a chic European dock.”

When you need a break from seafood, “Smokin Wolf not only has the best BBQ in East Hampton, but their quesadillas are delicious,” says Raya O’Neal, a manager at The Surf Lodge. “Their vegetarian Cowgirl Quesadilla tastes even better on the beach watching the sunset.” La Fondita in Montauk also serves up no-frills Mexican fare at outdoor picnic tables.

And if you’re just craving a slice, “Best Pizza & Dive Bar is the best joint on the east end,” says Attanasio. “Not only does it have the best ‘za in the area, it rivals the best grilled chicken parm hero in Montauk (or the city).”

Channing Daughters Winery
Channing Daughters Winery Courtesy Image

Where to Drink

Some of the best libations come out of the Hamptons—Channing Daughters Winery in Bridgehampton, Sag Harbor Rum, and Montauk Brewing Company all call the eastern end of Long Island home. And with hordes of New Yorkers flocking there on the weekends, you can bet there are plenty of places to imbibe. But skip the crowded deck at Surf Lodge and the spring breaker vibes at The Sloppy Tuna for the spots the locals prefer.

“Lynn’s Hula Hut is one of Montauk’s best kept secrets for a great cocktail in a laid-back environment,” says Filopoulos. It’s literally in the middle of a parking lot, and tends to draw a mostly local crowd. “They’re also big supporters of the town’s arts community and regularly showcase local talent. Try the Hula Juice!”

Memory Motel, Montauk
Memory Motel, Montauk Courtesy Image

If you’re not up for the crowds at the popular sundowner spot Navy Beach, “Montauket is another fun bar scene that’s a bit younger and has great water views,” says Heyn. The family-owned, cliffside bar and restaurant sits on prime sunset territory on a grassy bluff overlooking Fort Pond Bay. It draws year-rounders and summer regulars.

For those who can’t get over all the 20-somethings flooding the bars, “the Crow’s Nest seems to have a more relaxed vibe and a slightly older scene than Surf Lodge and Gurneys, and doesn’t seem to ever be as packed,” Heyn adds. There’s a panoramic view of Lake Montauk from the deck, and also a fresh farm-to-table menu, if you want to stay for a meal.

And for later, there’s the Memory Motel, a dive-club in Montauk with tons of history and pop culture clout. The space was the inspiration for The Rolling Stones song of the same name.

The Point
The Point Courtesy Image

Where to Chill

Above all, the Hamptons are meant to be a beachy escape from hectic city life. So if you want nothing to do with the “scene,” there are plenty of ways to zen out—starting at the actual beach.

“Two Mile Hollow Beach in East Hampton is a great beach for non-locals,” says Bryan Fedner, co-founder of StayMarquis, a full-service vacation rental company in The Hamptons. While parking is $30, it’s totally worth it for the picturesque oceanfront views and clean sand.” Parking is $40 at Cooper’s Beach in Southampton, he adds, but it’s another quiet beach with chair and umbrella rentals, as well as refreshment stands for those who want to avoid the summer crowds at the rowdier beaches.

“Kirk Park Beach in Montauk is a great spot for non-locals with free parking and an awesome surf scene,” says Fedner. Meanwhile, “lots of locals head to Ditch Plains to surf, and Air + Speed Surf Shop offers surfing lessons for adults as well as a really great surf camp for young kids, so the whole family can spend the day together at the beach,” says Filopoulos.

Off the beach, you can head to The Salt Cave in Montauk, which O’Neal calls “a hidden gem.” “If you’re dealing with any aches, pains, or ailments, an hour-long session in the salt cave will do your body some good,” she says. “Anyone can benefit from this, and it’s really great for those who are health-conscious.”

Fitness-minded vacationers may want to skip the packed Soul Cycle studios and head to JB Studio in Montauk for yoga and meditation or Silich Core and Strength in East Hampton for TRX, rowing, and HIIT classes. For runners and walkers, Fedner recommends the Cedar Point Lighthouse Loop Train near East Hampton. “It’s an awesome 5.3-mile loop near the water,” he says—and it’s dog-friendly.

If you’d rather be active on the water, Khanh Sports in East Hampton and Bridgehampton offers gear rentals including surfboards, paddleboards, and kayaks for hourly and daily rates, while Sag Harbor Sailing offers sailboat rentals, private charters, and sailing lessons in the heart of Sag Harbor.

There’s also a thriving arts scene. Stop by the LongHouse Reserve, a beautiful outdoor art museum with sculptures and gardens. Or, head to the Pollock-Krasner House, which was formerly Jackson Pollock and Lee Krasner’s home; it now serves as a public studio and gallery space. “Check out Guide Hall in East Hampton, where the calendar of events includes everything from movie screenings to lectures to live music,” says Fedner.



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