Best Things to Do in Montauk and the Hamptons: How to Experience Long Island Like a Local

No one would argue the Hamptons are a scene. When New York City empties out on summer weekends, you can bet majority of them are headed to the towns, villages, and hamlets along the East End of Long Island. With vineyards and beaches ripe with surfing, there's no shortage of things to do in Montauk, East Hampton, Southampton, Bridgehampton, Amagansett, and Sag Harbor. It's one of the best vacations in the U.S., after all, and makes for a killer bachelor party destination.

But if you want to beat the crowds and curate an experience that feels more authentic, heed these local recommendations.

When to Visit

Unlike Miami, which has a steady throng of tourists flocking to its shorelines year-round, the best things to do in Montauk and the Hamptons are relegated to the warmer months.

Peak season is June through September since many restaurants, hotels, and farmstands close for the winter. As such, crowds are heaviest mid-June through July. We'd argue the best time to visit Montauk and the Hamptons is September, when the number of visitors thins but the weather remains idyllic.

If you’re not a local (or a summer loyalist), it’s easy to get stuck on trendy spots that’ll empty your wallet and threaten your sense of personal space when tourism is at its peak. Here are our top recommendations.

Getting Here

If you don't have a car, you can get from New York City to eastern Long Island via the Hampton Jitney or the Long Island Rail Road. Just note you'll need to rely on Ubers and Lyfts to navigate.

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, East Hampton’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.

Sag Harbor

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.

Bridgehampton

Across the way in Bridgehampton, Room at the Beach is a former motel turned 10-room boutique hotel. 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.

Montauk

For a quieter weekend experience in Montauk, book a room at Marram. The oceanfront resort features cedar buildings, muted colors, and airy spaces that maximize the natural setting. It’s a calmer vibe than most Montauk mainstays and is a destination unto itself with morning yoga, nightly bonfires, and a surf program run by nationally renowned surfers from the area. Belly up to the counter at Mostrador Marram for craft cocktails, fresh-baked morning buns, roasted veg salads, and soft-scrambled eggs.

Gurney’s Montauk is the only year-round hotel in the Hamptons—and it has plenty to offer. Its Seawater Spa is a sprawling 30,000-square-foot space with plenty of opportunities to gaze out at the frothing Atlantic Ocean. You can do more than look, with direct access to the property's private beach. From here, you can book a court at Hither Hills Racquet Club (five-minute drive away) for morning tennis and partake in any number of monthly offerings like drive-in movies, mixology classes, and Montauk Music Festival (May 16-19).

East Hampton

Journey East Hampton is a boutique property sandwiched between Amagansett and East Hampton. Choose among 25 rooms that run the gamut from studio layouts to free-standing cottages, and relish the on-property saltwater pool, firepits, and complimentary bikes. You're within walking distance of luxury storefronts the likes of Prada and Chanel. But if it's a more grounding experience you're after, spend the day at the beach, then retreat to your hotel where Molton Brown bath products and Frette sheets await.

Where to Eat

Breakfast

Candy Kitchen in Bridgehampton is your classic diner experience (every beach town needs one).

You'd be remiss not to get a bagel while you're here—even if you're coming from New York City. Goldberg's has locations in Southampton, East Hampton, Montauk Village and Montauk Harbor, Sag Harbor, and more.

Joni's Kitchen in Montauk is a quirky fast-casual spot to nab a breakfast burrito or a smoothie before popping next door for espresso or cold brew from Left Hand Coffee.

Lunch

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).”

Related: Lobstering, Rare Beer, and Sunset Surfs: Four Days in Portland, Maine

In Montauk, it’s all about the views, and George’s Lighthouse Café is a great vantage point come sunset. The café—which serves a casual seafood menu—is open from 10 a.m. through sunset, and sits right on the water.

“One of my family’s favorite spots for dinner is Inlet, down by the entrance to the harbor near Montauk Airport,” says George Filopoulos, owner of Gurney’s Resorts. “They serve terrific sushi and offer equally amazing views of sunset.”

Dinner

Speaking of Gurney's, the Montauk location is another excellent basecamp to take advantage of the best things to do on the East End. Scarpetta Beach, the beachside counterpart to the downtown Manhattan restaurant, offers up housemade pasta, fresh seafood, and seasonal offerings. The Negroni Mediterraneo, seared scallops, black cod, and espresso budino dessert make for a perfect meal.

You can lose hours waiting for a seat at the most popular spots, 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. 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.

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. Skip the crowded deck at Surf Lodge and the spring breaker vibes at The Sloppy Tuna for spots 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!”

Editor's note: Lynn's Hula Hut is changing locations for Summer 2024; stay tuned for its new location.

If you’re not up for the crowds at the popular sundowner spot Navy Beach, “The 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 Gurney's, and doesn’t seem to 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.

For post-dinner drinks, head to 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.

If you're eating at Gurney's, check out the property's Lounge for cocktails. Last summer, the property partnered with Patrón for an El Cielo takeover on the East Deck. The tequila lounge had bespoke libations like Patrón El Cielo Royale, El Cielo Ginger Spritz, and Patrón Reposado Spicy Paloma.

Things to Do in Montauk and the Hamptons

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.

Beaches

“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.

Wellness and Fitness

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; 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.

No matter the season, book a spa treatment at the Seawater Spa at Gurney's. Indulge in a Bespoke Deep Tissue Massage or the deeply relaxing Deep Sea OSEA Undaria Massage, which ends with a face and scalp massage. After, visit the BathHouse and switch between hold and cold therapy with a steam room, sauna, hot plunge, and cold plunge. The property's unique seawater pool is fed directly by the Atlantic Ocean.

Art and Culture

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.

Why You Should Trust Us

Ashley Mateo and Brittany Smith are lifestyle journalists with a combined 20 years of experience covering travel, hospitality, and wellness. Smith, Men's Journal's deputy editor, is also a Long Island native. In addition to generating this travel guide from personally experiencing these places, locals and other experts were tapped to provide additional advice.