As a Long Islander, I rarely make it out to the Hamptons. It’s like if you live in New York City you never go to the Statue of Liberty—I’ve always considered the Hamptons (especially in summer) a tourist attraction, and not really worth the crowds. In the past few years, I’ve gone out to Montauk a couple of times in the fall to get away for a bit and enjoy the quiet. But when I booked a trip to the Hamptons this October, I found something I definitely didn’t expect to find—it wasn’t that quiet. Everything was open!
Because more and more people have moved out East this year, the shops, restaurants, and even hotels are remaining open year-round, rather than closing for the season by late September. While I hadn’t anticipated such a lively weekend, it really was a welcome surprise, and it certainly makes the Hamptons an excellent getaway from NYC (even though it’s not beach season).
Where to stay in the Hamptons
The Roundtree Amagansett
Book now: from $395 per night, theroundtreehotels.comThe Roundtree is the ultimate off-season Hamptons spot. Centrally located right on Main Street in Amagansett, the boutique hotel is within walking distance of many shops and restaurants, allowing you to enjoy the upscale, small-town feel of the Hamptons, without being so close to the beach that you’ll feel the cold wind off the ocean this time of year.
The accommodations range from luxury rooms to one-bedroom suites to three-bedroom full cottages. The complimentary minibar comes stocked with beverages and local snacks, and continental breakfast is included (which you can have outdoors or as room service). Particularly fun, especially in colder months, is the s’mores happy hour held nightly (weather-permitting) on the expansive two-acre property.
Just over one mile from the Atlantic Ocean, the Roundtree is surrounded by tranquil farmland, but if you do want to go to the beach, the hotel will provide beach cruiser bicycles at no additional cost. Usually, it will also provide a beach parking pass so guests can drive to the beach (although due to COVID-19 restrictions, only Hamptons residents could park at beaches during the 2020 season).
Shou Sugi Ban House
Book now: from $975 per night, shousugibanhouse.comLocated in Water Mill, between Southampton and Bridgehampton, Shou Sugi Ban House opened its doors last year. This spa and retreat consists of 13 guest studios with private garden patios, a treatment spa with roof deck, and two repurposed barns (one with a demonstration kitchen and another with a tea bar)—all run on solar and geothermal power.
Insisting it offers “the only comprehensive wellness program” in the Hamptons, the hotel has a resident nutritionist to design a seasonal menu that’s vegetable focused and locally sourced, as well as guided wellness rituals, including sound healing, tea traditions, aromatherapy, and a wealth of spa treatments.
Things to do in the Hamptons in the off-season
Although Long Island’s North Fork is better known for its wineries, the South Fork holds its own.
Wölffer Estate Vineyard has a tasting room (by reservation only), but is also available for drive-through wine pickup. Yes, you read that right. You’ll see its bright pink sign from down the road, and simply pull in, follow the cones, and find yourself at a chalkboard menu from which you can select the type of wine (or cider) that you might like to bring home. The Estate also has a restaurant in Amagansett, Wölffer Kitchen, serving up local, seasonal cuisine and of course Wölffer Estate’s award-winning wines.
Duck Walk, founded in 1994 and one of the more well-known Long Island wine brands, has full vineyards with tasting rooms on both the North and South Forks. Encompassing over 140 acres overall, Duck Walk produces over 5,000 cases of different kinds of wine each year, including specialties like ice wine and blueberry port. Reservations are available for groups of 6 to 10 people.
Channing Daughters Winery has six separate vineyards on its Bridgehampton farm, and it grows and creates over two dozen types of wines, from cabernets to chardonnays to sparkling merlots. The grounds also include a sculpture garden and a tasting room. This year, the tasting room is closed due to COVID, but individuals are welcome to call ahead to pick up wine. Considering itself a “vineyard with a purpose,” Channing Daughters prides itself on sustainability, recycling 100 percent of its grape pomace (leftover skins, seeds, and pulp from each harvest) and using organic nitrogen sources like its own farm-made compost; it is a founding member of Long Island Sustainable Winegrowing.
Explore the art scene
The Hamptons are an excellent place to see art, particularly the art of those who have called Long Island home. Aside from the many galleries that can be found on Main Streets throughout the Hamptons, there are museums that shouldn’t be missed:
Parrish Art Museum is home to works from artists like Chuck Close, Lee Krasner, and Jackson Pollock. Throughout the pandemic, the museum is highlighting the stories of more than 100 current East End artists.
The Dan Flavin Art Institute, housed in a former fire station, was established in 1983 to showcase artist Dan Flavin’s signature works of fluorescent light. Nowadays, the Institute continues to display 9 of Flavin’s works as well as rotating exhibitions of Long Island artists’ works, most recently an immersive installation by Jill Magid consisting of 11 screen prints that interact with Flavin’s fluorescent lights.
Where to eat & drink in the Hamptons
The Lobster Roll
A Hamptons institution since 1965, the Lobster Roll (also known as LUNCH thanks to its iconic sign) is an easy stop along the way out East. With both indoor and outdoor seating, the casual restaurant is a popular spot for lunch, dinner, or cocktails. As the name suggests, the restaurant specializes in hot and cold lobster rolls as well as a wide variety of local seafood, and it embraces a nostalgic “seafood shack” vibe.
The Hamptons in the off-season is not a hot and sunny experience. It’s an extremely cozy experience. And nothing warms my soul like a big cheese-covered bowl of french onion soup—except maybe a great burger. Rowdy Hall, located in East Hampton, has both. One of the more down-to-earth eateries the Hamptons has to offer, the restaurant is a delightful mix between an English pub and a French bistro, and comes complete with an extensive drink menu (to really warm your soul) that includes local beers and wines from the East End.
Montauk Bake ShoppeThough not technically part of the Hamptons, Montauk Bake Shoppe is worth the 20-minute scenic drive on NY-27. Serving both lunch and breakfast, the bakery is a solid option for a quick, light bite, but the absolute gem of Montauk Bake Shoppe is the jelly croissant. Flaky on the outside and filled with jam on the inside, it gives off Cronut vibes . . . except it’s better. Trust me.
How to get to the Hamptons from New York City
By car: Take the I-495 to exit 70, and head south. Follow signs for NY-27 E toward Montauk. The trip takes about 2.5 hours.
By train: Take the Long Island Railroad Babylon Line from Penn Station and transfer to the Montauk train at Babylon. The trip takes about 3 hours. During the summer there is an express Montauk train from Manhattan. Schedule information: mta.info.
By bus: Take the Hampton Jitney Montauk Line Eastbound from Manhattan, about 2.5 hours. Off-season schedule information: HamptonJitney.com.