In the summer, the North Fork of Long Island is overrun with well-heeled New Yorkers enjoying their home away from home — the Hamptons. From Water Mill to Montauk, vacationers flock to white sand beaches, wineries and relaxed restaurants to get away from the NYC heat.
But the Hamptons isn’t just an attractive getaway in July and August. In fact, we prefer to visit in shoulder season (May, June, September and October), when shops are still open, temperatures are mild and thinner crowds mean you can actually head from south to east without an hour-long backlog on Route 27.
Here are 10 of our must-dos, all year long.
Dine Out…Or In
Dining out is one of the best ways to see and be seen in the Hamptons, and the fun starts with breakfast. We prefer a more casual affair — a flagel (get the sunflower seed variety of the flattened bagel) from local favorite Goldberg’s in Montauk.
Choose your destination for dinner: we love the burgers at Almond and the heirloom kale salad at Forbes Travel Guide Four-Star The Topping Rose’s Jean-Georges in Bridgehampton, the fresh Greek fare at Calissa in Water Mill and the must-have zucchini fritti at Nick and Toni’s and the patio at Dopo La Spiaggia in East Hampton.
And when it comes to sweets, nobody does it better than Main Street’s Scoop du Jour.
Day trip to Shelter Island
We love the Hamptons, but sometimes you just want to escape the crowds. Hop the car ferry to Shelter Island for the day, where you can unplug and relax in nature (one-third of the island is a preserve).
Party It Up in Montauk
There’s no better place for dancing than at Montauk’s The Surf Lodge, a popular spot for live music with the 20- and 30-something crowd out from New York for the weekend. Expect concerts from names like Wild Belle, Oak and Ash, Lupe Fiasco, Jenny Lewis and more.
It’s definitely a party atmosphere, but the outdoor ambience and laid-back vibe make this destination a perennial summer favorite.
Spend the Week
If you’re spending a few nights in the area, you simply can’t go wrong with a stay at Topping Rose House, a 22-room stunner in Bridgehampton with a great art collection and a traditional-modern aesthetic from well-known designer Alexandra Champalimaud.
Hamptons icon Gurney’s Montauk Resort & Seawater Spa is the only Montauk hotel to remain open all year round. A head-to-toe renovation at the oceanfront hotel introduced a beachy-chic vibe that you simply have to see.
Jedediah Hawkins Inn is a nearby treasure (Jamesport sits about 35 minutes from the Hamptons), but the six-room, Forbes Travel Guide Recommended inn more than stands out for its quirky charm.
We also like the intimate Mill House Inn, a tiny 10-room retreat known for its incredibly sumptuous breakfast — yes, there’s lobster involved.
The idyllic Inn at Windmill Lane in Amagansett makes for a relaxing stay, where butlers prep your wood-burning fireplace and you can bliss out in oversized tubs stocked with Molton Brown amenities.
Shop Till You Drop
There’s no shortage of high-end shopping in this luxe area, but South and East Hampton have the best streets for one-stop designer browsing.
In East Hampton, peruse everything from high-end workout gear at Sweaty Betty to boutique finds from designers like Jimmy Choo, Theory, Zimmermann and more.
Walk the Beaches
With so much to do, it’s easy to forget that Long Island offers dozens of public stretches of sand (though check with your hotel on beach permit requirements; each hamlet has its own rules). Coopers Beach in Southampton presents a fantastic spot for a scenic stroll past some beautiful high-end homes in the Hamptons (hello, house from Billions!).
The more active set might prefer to grab a bike from Amagansett Beach & Bicycle Company and cruise along Highway 17 until you reach the Montauk Lighthouse.
Hit the Surf
If biking and sunbathing are too low-key for you, head to Montauk’s Ditch Plains Beach where you’ll find some of the best waves in town, perfect for longboarding experts and newbies alike.
If that sounds a bit intense, make your way to Three Mile Harbor for a lesson with the top stand-up paddleboarding instructor in the area, the Paddle Diva. After you’ve worked up an appetite, grab a quesadilla from cult favorite food truck Ditch Witch.
Wine a Little
Nobody does warm-weather sips like Sagaponack’s Wölffer Estate Vineyard. This 55-acre winery makes it easy by offering sparkling, still and even rosé cider varietals, plus an adorable drive-through option that lets you pick up a case on the way home. Or simply park yourself on one of the cozy lounge chairs and enjoy a cheese plate with a glass of vino.
If you’re not a wine drinker, head to Montauk Brewing Company, where you can sample all seven varieties of this local ale. The summery watermelon beer is a refreshing seasonal pour.
Get Your Workout In
This is a town that thrives on looking its best, so it should come as no surprise that the Hamptons doesn’t lack for spots to get in some fitness. From Flywheel to SoulCycle to Tracy Anderson and Exhale, all the top facilities have outposts in the area, leaving you no excuse to miss a workout — even NYC-based Class Pass comes out each summer.
It isn’t all parties, shopping and beach time — the Hamptons also has great options to experience the local culture, from seasonal antiques and arts festivals to worthy museums and galleries. One of our favorites is the Pollock-Krasner House, a museum that was once the home of painter Jackson Pollock and his wife and fellow artist, Lee Krasner. Tour the house, which still has many of the original furnishings.
You’ll also want to plan an afternoon at the LongHouse Reserve in Northwest Woods, where you’ll find 16 acres of landscaped gardens and installations by names like Willem de Kooning, Dale Chihuly and Yoko Ono.