The Ultimate Hamptons Summer Guide

Leah Bourne
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The Ultimate Hamptons Summer Guide
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The Hamptons, the storied enclave on the eastern tip of Long Island in New York, has long been considered a summer paradise. We’ve broken down the five towns to know—Southampton, Bridgehampton, Sag Harbor, East Hampton, and Montauk—and highlighted the best of where to eat, shop, and party, so you can vacation like a local all summer long. From where to score the ultimate lobster roll, to the museum’s and beaches that should make your cut this summer, our picks aren’t to be missed.
Have a favorite spot in the Hamptons? Share your pick in the comments below.
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The Hamptons, the storied enclave on the eastern tip of Long Island in New York, has long been considered a summer paradise. We've broken down the five towns to know—Southampton, Bridgehampton, Sag Harbor, East Hampton, and Montauk—and highlighted the best of where to eat, shop, and party, so you can vacation like a local all summer long.

SOUTHAMPTON

Distance From NYC: 1 Hour and 45 Minutes

Known For: Often called the "old money" Hamptons, the town, founded in 1640, is still home to some of the most incredible and over-the-top estates on Long Island. 

Famous Residents: George Soros, Rachael Ray, and Tory Burch, all call Southampton home.

WHERE TO EAT

Head to Silver's Restaurant (15 Main Street; silversrestaurant), only open for lunch, to try their signature BLT and lobster roll. For dinner, opt for Gabby Karan's Tutto Il Giorno (55 Nugent Street; 631-377-3611) where you can't go wrong ordering the papardelle with bay scallops or the poached Branzino. In need of an afternoon snack? Stop by Sant Ambroues (30 Main Street; santambroeus.com) for a cup of gelato and a espresso. Want to eat where the chefs eat? A few minutes by car from the town of Southampton is the much buzzed-about new upscale Chinese eatery Red Stixs (pictured, 1020 Montauk Highway; redstixs.com). Already a favorite of the likes of Eric Ripert, don't leave without ordering the lettuce wraps and pork soup dumplings.  

Photo Credit: Rob Rich/SocietyAllure.com.

WHERE TO SHOP

While there are plenty of high-end chain stores in Southampton including Ralph Lauren and Calypso St. Barth, the individual boutiques are worth checking out too. At Tenet (pictured, 91 Main Street; tenetshop.com) expect designers including A.P.C. and Robert James. At the concept store James Fairchild (619 Hampton Road; jamesbfairchild.com) expect everything from vintage Birkins to antique Coco Cola signs. And at the Topiaire Flower Shop (51 Jobs Lane; 631-287-3800) hunt for the perfect bouquet, specialty soaps, and hand-painted signs to decorate your summer cottage with.

WHAT TO DO

Southampton boasts some of the most beautiful beaches on the East End including Coopers Beach (268 Meadow Lane). If you aren't a town resident just be prepared to pay $40 per day to park your car. Looking to do something a tad more adventurous? Learn how to play polo at the Southampton Hunt & Polo Club (pictured, 206 Millstone Road; southamptonpolo.com), which has programs for novices and intermediate players.

WHERE TO PARTY

Sit poolside with a cocktail at BLT Steak at the Capri (39A Route 27; caprisouthampton.com) while watching the sun set. For late night revelry head to Southampton Social Club (pictured, 256 Elm Street; southamptonsocialclub.com) where the crowd gathers outside by cabanas until the wee hours.

BRIDGEHAMPTON

Distance From NYC: 2 Hours

Known For: Home to the Hampton Classic (the horse show of the summer) and Bridgehampton Polo, this town is known for its quaint restaurants and boutiques.

Famous Residents: Kelly Ripa, Matt Lauer, Sarah Jessica Parker, and L.A. Reid all call Bridgehampton home.

WHERE TO EAT

Pierre's (pictured, 2468 Main Street; pierresbridgehampton.com) has been a Bridgehampton standby for years thanks to its perfect Parisian bistro fare. Order from the rotating list of daily specials and you won't be sorry (the Bouillabaisse Marseillaise served on Fridays should not be missed). Another iconic Bridgehampton restaurant, though far less formal, is the Bridgehampton Candy Kitchen (2391 Montauk Highway; 631-537-9885). This classic diner and ice cream parlour hits the spot perfectly after a long day at the beach.

WHERE TO SHOP

At design mecca Maison 24 (pictured, 2424 Montauk Highway; maison24.com) expect everything from cow hidepillows to Alexandra von Furstenber's lucite treasure boxes to Geoffrey Bradfield designed Louis chairs. Naturally, if you have to check prices, this isn't the store for you. The Antique Shop (2466 Main Street; 631-537-3838) is one of the true hidden treasures of the Hamptons. Inside, find wares from three distinct antiques dealers, including the most impressive selection of vintage Chanel costume jewelry just about anywhere. At JoanMarie (2462 Main Street; joanmarieshoes.com) you'll find a mix of summer appropriate shoes from the likes of Tila March and Tuccia Di Capri.

WHAT TO DO

At the Loaves & Fishes Cooking School at the Bridgehampton Inn (pictured, 2266 Main Street; landfcookshop.com) learn how to make summer favorites like lobster and halibut salad or take a tutorial class on how to grill. Visit the Parrish Art Museum (279 Montauk Highway; parrishart.org) which just opened the doors to its new 34,400-square-foot Herzog & de Meuron-designed building. Its permanent collection includes artists like Roy Lichtenstein, Cindy Sherman, and Willem de Kooning that also have a Hamptons connection. The Bridgehampton Farmers Market (151 Mitchells Lane) on Fridays from 3 to 6:30 p.m. boasts produce and plants, hyperlocal Wölffer wine, David Falkowski's mushrooms, and coffee from Turtle Island.

WHERE TO PARTY

Bridgehampton is low-key, so don't come here searching for velvet ropes and all-night ragers. A new hotel Topping Rose House (pictured, One Bridgehampton Sag Harbor Turnpike; toppingrosehouse.com) popped up in a Georgian mansion on the edge of town, and we recommend grabbing a seasonally-inspired cocktail from the bar and taking it out to the wrap-around porch for a nightcap. It is the perfect way to end a Hamptons evening. 

SAG HARBOR

Distance From NYC: 2 Hours and 15 Minutes

Known For: Mentioned repeatedly in Moby-Dick, this Hamptons town sits directly on the water.

Famous Residents: Jimmy Buffett and Richard Gere have homes in Sag Harbor.

WHERE TO EAT

Some of the best sushi and Japanese inspired dishes on the East End can be found at Sen (pictured, 23 Main Street; senrestaurant.com). Favorites include seafood ceviche and miso sea bass, but you truly can't go wrong. The Cuddy (29 Main Street; 631-725-0101) by the same owners as Sen, is a gastropub with inventive cocktails, microbrews, and boutique wines. The sea scallops over grits with yellow curry is a can't miss dish from the menu. At Harlow East (Long Wharf at Bay Street; harlownyc.com) head straight for oyster and crudo bar, which you can enjoy while enjoying the waterfront, and gawking at the parked yachts. 

WHERE TO SHOP

At design store MONC XIII (pictured, 40 Madison Street; monc13.com) scoop up anything and everything from Hermès plates to a leather wrapped ice bucket by Sol Y Luna. At Duck & Weave (78 Main Street; duckandweave.co), former fashion photographer Robin Saidman sells perfect button-downs made in New York City's Garment District. And at Sylvestor & Co. (103 Main Street; returntomainstreet.com), which calls itself a "contemporary general store," stop in for kitchen gear, pre de provence soap, and even coffee and ice cream by Dreamy.

WHAT TO DO

Sag Harbor is all about its maritime history. Visit The Sag Harbor Whaling Museum (200 Main Street; sagharborwhalingmuseum.org) to learn about what makes the town so special. Enjoy the water up close with a sailing lesson at Sag Harbor Sailing (pictured, 51 Pine Neck Avenue; sailsagharbor.com) starting at $275 for a half-day charter.

WHERE TO PARTY

Bars in Sag Harbor come with just the right amount of history. At The American Hotel bar (pictured, 49 Main Street; theamericanhotel.com), a landmark built in 1846, command a backgammon board and order a Manhattan from longtime bartender Vinnie Rom. Head to dive bar Murf's BackStreet Tavern (64 Division Street; murfstavern.com) to hang with the locals while drinking beer and playing the ring toss game. 

EAST HAMPTON

Distance From NYC: 2 Hours and 15 Minutes

Known For: If Southampton is the "old money" enclave than East Hampton is very much the "new money" destination. Stroll along Main Street here, and you can easily feel like you're in New York City thanks to outposts of Tiffany & Co. and Ralph Lauren. Luckily, the town also boasts some of the beautiful beaches on the East End.

Famous Residents: P.Diddy, Gwyneth Paltrow, and Martha Stewart all have homes in East Hampton.

WHERE TO EAT

Nick & Toni's (pictured, 136 North Main Street; nickandtonis.com) is the table to get during the summer months in the Hamptons. The restaurant's house made ricotta and its signature risotto can't be beat. Another plus? You truly never know who you will be sitting next to here, be it a Clinton or Barbara Walters, which is half the fun. The Palm (94 Main Street; thepalm.com) is another East Hampton classic (the summer lobster dinner for two for $79.95 is a rare Hamptons deal). For a casual dining experience opt for The Blue Parrot (33 Main Street; blueparroteasthampton.com) for a killer pitcher of margaritas and lobster tacos.

WHERE TO SHOP

The main drag in East Hampton could easily double for an exclusive shopping street in New York City. Forget the chain stores and head to some of the more original offerings like Blue & Cream (pictured, 83 Main Street; blueandcream.com) for a mix of designer duds from the likes of Alexander Wang and Charlotte Ronson. At The Monogram Shop (7 Newton Lane; themonogramshops.com) you can get practically anything monogrammed from a coffee mug to a bath robe (this is a great spot for gifts). Another favorite is the old school White's Chemists and Perfumers (81 Main Street; whiteeasthampton.com) which stocks hard to find skincare, makeup, and haircare brands.

WHAT TO DO

For art enthusiasts the Pollock Krasner House & Study Center (pictured, 830 Springs Fireplace Road; pkhouse.org), the former home of Jackson Pollock and his wife Lee Krasner is a can't miss. Consistently ranked as "America's Best Beach," Main Beach (10 Ocean Avenue) in East Hampton is as picturesque as it comes. Take note: only those with beach passes can park at this beach on the weekends.

WHERE TO PARTY

Head just east of East Hampton to the town of Amagansett to The Stephen Talkhouse (pictured, 161 Main Street; stephentalkhouse.com) for live music and the perfect casual night-out. The crowd is the perfect mix of weekenders and locals. Looking to hang with the young and gorgeous? Moby's (341 Pantigo Road; 631-527-5388) is new to the Hamptons scene, opened by Aussies Nick Hatsatouris and Lincoln Pilcher, who own the Eveleigh in L.A. Settle into the back communal area with a signature cocktail for the perfect cap to your night out east. 

MONTAUK

Distance From NYC: 3 Hours

Known For: This surfer's paradise has morphed in recent years into a massive hipster hangout—food trucks, fedoras, and all.

Famous Residents: Ralph Lauren, Cynthia Rowley, and Robert De Niro call Montauk home.

WHERE TO EAT

Considering that Montauk is a hipster destination, it is no surprise that its restaurant scene is cooler than cool. At The Crow's Nest (pictured, 4 Old West Lake Drive; crowsnestmtk.com) expect Mediterranean-inspired seafood and water views. Dave's Grill (468 West Lake Drive; davesgrill.com) is a Montauk institution. Order the lobster roll made with a half-pound of knuckle and claw meat, and served on a toasted brioche. Take note that reservations can only be made day-of. At Navy Beach (16 Navy Road; navybeach.com) expect nautical decor, plenty of fresh seafood, and one of the best burgers on the East End.

WHERE TO SHOP

Scoop up gorgeous dresses, shorts, and skirts made with vintage fabrics and beading from Peri Allen (206 Essex Street; 516-658-9121) a favorite of Gwyneth Paltrow. At Surf Bazaar (183 Edgemere Street; thebazaarshops.com) scoop up supper favorites like the perfect beach ready tunic to embroidered caftans. 

WHAT TO DO

Since Montuak is renowned for its surfing, why not take a surf lesson? The Eastend Surfing School will set you up with an instructor at the famous Ditch Plains beach (pictured, Montauk Peninsula; eastendsurf.com), so you might actually have the hope of catching a wave. Another can't miss Montauk activity is visiting the famous Montauk Point Lighthouse (2000 Montauk Highway; montauklighthouse.com).

WHERE TO PARTY

Its tagline is "it's like summer camp with cocktails" which is why the in-crowd can't get enough of Ruschmeyer's (pictured, 161 2nd House Road; kingandgrove.com). Hang out at the Blackwell Rum Shack bar or in one of the backyard teepees (we kid you not). The Surf Lodge (183 Edgemere Street; thesurflodge.com) continues to be equally "scene"-y thanks in no small part to its views of Montauks' Fort Pond. Hang out with the locals at The Montauket (88 Firestone Road; montauksun.com) known for its view and strong cocktails. 

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