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Every summer, New Yorkers flock eastward in search of the best towns with sea breezes, sandy shores, and a slower pace. Enter: the Hamptons, a stretch of Long Island’s East End that feels worlds away from New York City (though a conservative estimate is a three-hour drive from Manhattan). And while yes, the Hamptons are widely known for being a vacationland for the city’s richest residents, we’re here to prove that’s only part of the story—and there plenty of options for travelers of all kinds.
Whether it be laid-back days in Amagansett, designer shopping in Bridgehampton, or catching a wave in Montauk, you’ll find an ideal pocket with natural beauty and lots to do—no matter your style of summer escape. This guide takes you on a walk through the Hamptons’ most beloved hamlets, beach towns, and hidden gems, with insights on the best dishes, hotels and Airbnbs, and places to see while you’re there.
Read on for an ultimate roadmap to the East End of New York State, compiled by two native New Yorkers who return to the North and South Fork each summer. Here’s how to live out your summer dreams in towns that do laid-back luxury just right.
FAQ:
When is the best time to visit the Hamptons?
While summer is obviously when the magic happens, we’d be remiss not to mention some more specifics here. If your goal is to chill, visit during the week if you can, or even on a Sunday. Fridays and Saturdays will consistently be the busiest—and look out for holiday weekend crowds, in particular. That doesn’t mean you should shy away from the weekends entirely—just be strategic, and think before you book.
If you’re thinking of visiting in the off-season, do it. (Just note you’ll probably need a car, as transportation options like Uber become sparser, and you’ll want to look online to be sure you’re headed to places that haven’t closed for the off-season.) The North Fork is full of wonderful wineries and vineyards, while Water Mill and neighboring towns have pumpkin patches, seasonal sweet treats, cider tastings, and all the other fall festivities you could dream of. Keep in mind, too, that as seasons have started shifting, September is still a warm month, and even October is full of crisp, pleasant weather.
How do I get to the Hamptons from NYC?
- Take the Long Island Rail Road (LIRR) from NYC’s Penn Station or Grand Central Station and transfer at Jamaica Station (a few trains have a direct option from Penn Station throughout the summer, too).
- Rent a car: This is a great, reliable option if you plan to drive between towns.
- Take the Hampton Jitney from Manhattan or the Queens Airport Connection stop in Fresh Meadows (tickets are cheaper when you buy in advance, rather than day-of).
Jump to:
Poolside at Seven Beach Lane, a conveniently located hotel in Westhampton
Liz Clayman/Seven Beach Lane
Westhampton
Best for: A low-key weekend in an up-and-coming town
The westernmost of the bunch, Westhampton has sometimes been thought of as less luxurious than its fellow Hamptons towns. Let us debunk this myth once and for all, though, because Westhampton has gotten a serious glow-up in the past two years, with new hotels, new restaurants, and even a new giant windmill popping up in the center of town. Last summer saw the opening of Seven Beach Lane, a boutique hotel perfectly situated between the beach and town, and this summer, Three Ducks, an old motel turned chic stay, is making headlines, part of a new wave of Hamptons motels making a statement post-renovation. It seems like people are finally catching on to the fact that being the closest to the city is actually worth bragging about.
Start your day at Doza Yoga in town for a hot summer flow, but make sure you book in advance as classes fill up pretty quickly on the weekends. For food and drink, stick with morning classics like family-run Goldberg’s (not to be confused with the chain throughout the rest of the Hamptons), for bagels, or Beach Bakery for a pastry (get the croissant jelly roll), but try out newbies like Flora and The Ivy for dinner. Shock Ice Cream and Kaleidescoops will satisfy your sweet-tooth for dessert, and rest assured that you can shamelessly stroll around in your sweats in this neck of the woods. Our favorite Westhampton nightcap is a sunset stroll on Roger’s Beach (read: there’s no party scene, but it probably won’t bother you), which is free to the public after 5 p.m. And if it’s still light out post-walk, drive along Dune Road to sneak a peek at some absolutely stunning houses nestled between the beach and bay.
Where to stay in Westhampton:
Along the vineyards in the North Fork of Long Island
Greg Bethmann/Getty
North Fork
Best for: Prancing around vineyards in an unpretentious scene
Ah, the underrated and slightly forgotten about North Fork (if you’re not familiar, Long Island splits in two when you reach far enough east: the South Fork is home to The Hamptons, and the North Fork is its northern counterpart). Yes, it’s a little quieter here, and no, you are not technically in the Hamptons, but the North Fork has plenty to offer and has recently become a popular spot for group trips (read: bachelorette parties) in the off-season due to its impressive vineyard, farm, and winery scene. And if you’re a rosé lover, you’re in luck: Croteaux Vineyards is the only vineyard in the US dedicated exclusively to making fruity rosé wines. In terms of where else to explore, head to the village of Greenport for great food, shops, and overall proof of life, or Riverhead, which is home to the Tanger Outlets (worth going!), several chain restaurants, and your classic Targets and the like. Southold is another popular nearby town, where you can visit the Horton Point Lighthouse and Museum, as well as Sparkling Pointe Vineyards & Winery.
