The Hamptons Is Now a Year-Round Playground—Here's What to Expect

Amanda Villarosa

Long waits at the hottest restaurants, schools filled to capacity, sold-out SoulCycle classes en plein air.

Year-round residents of the Hamptons have long called the day after Labor Day Tumbleweed Tuesday. More sweet than bitter for them, it is the day when parking spaces become available for dry-cleaning and hardwarestore pickups. Anxious crowds interested in the $79-a-pound lobster salad at Citarella dissipate. Impossible reservations at the buzziest restaurants become available before 10 p.m.

And traffic becomes almost reasonable. “My favorite thing used to be watching the traffic leaving for New York on Sundays,” said Nancy Kane, a Southampton native who writes about Hamptons realty and notes that rentals are bleeding into January this year. “I would just sit on Main Street with a big bag of candy and laugh.” But on the Tuesday after Labor Day, I noticed no such easing up at Jean-Georges in Bridgehampton. Not-so-sparsely-spaced diners on the white-columned wraparound porch of the Topping Rose House hotel were swooning over the sea bass and grilled lobster (to a soundtrack of crickets and plenty of nearby traffic) and seemed happy as, well, local clams.

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And why not? They weren’t back home in the city and likely weren’t going back. Instead, they were looking forward to enjoying the new tidal surge in fall activities from dining and shopping to art viewing, all blasting more oxygen into what had mostly been a seasonal summer-resort area. It has in recent years been morphing into a year-round region with a fall film festival and more private schools serving affluent work-at-home families, but this year the Hamptons season is extending into the fall and even the winter. For months, New Yorkers have been eschewing the city for outdoor activities, airy homes, and cars they don’t have to share. It’s no wonder that the other services and amenities they enjoy in the city have also moved out here.

Out-of-town guests, according to the Topping Rose House’s general manager, would be filling the hotel’s minimalist rooms for months ahead. Even the property’s celebrity trainers, who rival SoulCycle gurus, have signed on to lead outdoor yoga classes straight into heat-lamp season.


Yachts lined up in the Sag Harbor marina. Amanda Villarosa

“These days when I pick up my cell phone I just say, ‘Topping Rose reservations,’” said Christine Wächter-Campbell, one of the hotel’s owners and a Chelsea gallerist. “Getting a table for dinner is a challenge right now, but people have been so unusually grateful and patient.”

She thinks that the famously imperious population here has had a disposition upgrade after a summer of the worst health disaster to hit the country in a hundred years. “People out here got a reality check that being able to eat out or stay in a hotel is a privilege not to be taken for granted,” she continued.

The Hamptons, in fact, have made all kinds of adjustments around the pandemic, not just in mood but also in optimizing possibilities, including a first-time fall issue of Hamptons magazine (“Just in time for pumpkins and sweater weather,” writes its publisher). Of course, the changes that are making the area appealing beyond beach season aren’t for everyone. But while they may be a bummer for traffic haters, they are helping proprietors make up for the loss of income from last spring.

“Businesses are anticipating a longer selling season,” said Jesse Warren, the young Southampton mayor who owns two local fashion boutiques. “Moreover, many residents are realizing how beautiful Southampton is and how great a community we live in year-round, and they may likely stay because they are enjoying being here every day.”

The enjoyment had been of a more sequestered nature when I visited Southampton back in May. Talk about a tumbleweed town. At the Long Island Rail Road station on a Friday, typically the scene of an onslaught, I watched as a train arrived from Manhattan and only two young people got off. A black Range Rover rolled up. A slender hand emerged from the window with two alcohol wipes. The visitors used them, then got in, and the car zipped away. I wondered what young people would do all summer to make up for the lack of weekend nightlife.

“By July 4th the public is going to demand that we reopen,” Ian Duke, the co-owner of Southampton Social Club, told me then. “That’s Independence Day, and people won’t stay in forever.”

Sure enough, by summer COVID-19 rules were relaxed for outdoor dining and shopping. Warren started his ambitious Southampton in the Streets, expanding the possibilities on Saturday nights. After that, major galleries—like flocks of shorebirds hovering over schools of bunker fish—followed their collectors, many of whom had declared that they weren’t going home to the city for months. With available retail space, why not?

Phillips auction house installed a show in the historic former Town Hall (more recently a Pottery Barn) with an eye-catching Jean-Michel Basquiat visible from the street. Hauser & Wirth opened next to the hot new Dopo Argento restaurant.


Art galleries along Newtown Lane in East Hampton. Amanda Villarosa

In East Hampton in August, following the arrival of Sotheby’s, with its lively shows of art, design, and jewelry, Guild Hall reopened with a blockbuster benefit show curated by artist Robert Longo that will be up through December. Pace Gallery opened over the summer too, helping to make East Hampton, with its Jackson Pollock House, Fireplace Project, Judith Leiber Collection, Eric Firestone Gallery, Drawing Room, and Tripoli Gallery, a mini art mecca.

“It’s not something I would have done,” Pace owner Arne Glimcher told the Wall Street Journal about his son Marc’s idea to open on Long Island. “East Hampton for me was about gardening, not art.” But if gardening is a type of cultivation, so is the seduction of new collectors. And as with all the other galleries and auction houses that moved in, exhibitions are slated to change more frequently than they do in the city to bring in foot traffic and create buzz.

Hannah Root, a Pace associate, told me that one silver lining to the pandemic “is that it brought more art out here, and people definitely want to see it.” That included the provocative and colorful work of leading Brazilian abstract artists Sonia Gomes and Marina Perez Simão, on display during my visit.

The same can be said for fashion. Armani recently opened a temporary boutique in East Hampton across from a Jimmy Choo pop-up, joining Kirna Zabête, Tory Burch, and Ralph Lauren to lure savvy shoppers. Tamara Mellon even opened a shoe truck to cruise the roads like something between a land shark and a Mister Softee. And in Southampton, Alvin Valley, the “King of Pants” for society women, opened a little shop for sending out racks of flirty ensembles on approval. “All my clients are here, and they’re not going back to the city, so I’m doing this for the rest of the year,” he said, citing society shopper swans Lourdes Fanjul, Aerin Lauder, and Marie-Chantal. “What else do I do with myself right now?”


Love Adorned, a shop in Amagansett Square. Amanda Villarosa

All over the East End, in fact, people are reimagining things. Bay Street Theater, for instance, opened an outdoor bar in Sag Harbor, where yachts with nowhere else to go crowded the marina, lines for village rental agencies spilled onto sidewalks, and the small but excellent school system took in several dozen city students. The theater presented a fall production of Moby Dick for students virtually, along with an online sing-along with top performers. It is also renting out the lobby for a quarantined first-grade classroom organized by pod parents. “We had to do something,” said Tracy Mitchell, the theater’s administrative director. “It’s all about figuring out how to deal with the change.”

In late August, when the roads were packed and public frustration with overextended cell service, beaches, and gourmet markets was peaking, I drove out to the Surf Lodge in Montauk for a dinner in honor of designer Jason Wu. The scene there—the typically packed restaurant and lounge had just a few civilized clusters—felt like a happy fantasy of resort living far from the fray. “We’re open for small dinner events and our hotel guests only,” Jayma Cardoso, the affable owner, told me. “It’s all super scaled-down and more thoughtful.”

In the time she had this spring not dealing with crowd control, concerts, and hotel turnover, Cardoso brought in the men’s designer George Sotelo of Thorsun to revitalize the Surf Lodge’s boutique. Renamed Concept Playa, it carries clothes, candles, and skin products, as well as Wu’s casual frocks. Wu’s cuisine was on the evening’s dinner menu too, including crispy tofu, stir-fried pea shoots, and sesame chicken salad. Since the onset of the pandemic, he’d been cooking elaborate recipes and posting them on Instagram.

“I never had four hours a day to cook before, and it’s been fun,” he said. “The whole slowing down of the fashion cycle has been good for the exhaustion we all were feeling.”

Cardoso, who also owns the Snow Lodge in Aspen, isn’t complaining either, although she worries about income. “We’re trying to figure out how to pay the bills to keep the lights on,” she told me. 

One idea: wellness weeks planned into the fall, with draws including celebrity vegetarian chef Adam Kenworthy and Melissa Wood Tepperberg, the Pilates, yoga, and meditation guru.

“It’s about an endless summer scenario for now,” Cardoso said.

The following day I drove into Amagansett and parked next to a Body Tech outdoor gym before padding around the village’s grassy main square. Designer Ulla Johnson’s fashion store sat next to busy Wölffer Kitchen, a dining outpost of the Wölffer Estate Vineyard in nearby Sagaponack. At Amber Waves Farm, which will have seasonal dinners this fall, I munched on a vegan summer roll and toured the fields of crops, with the required mask, of course. Jack’s, the coffee joint where I grabbed an espresso, had a line snaking out the door. Although it was a perfect beach day, Innersleeve Records also had customers. “I bet we’ll be busy all fall,” a manager told me.

Amagansett had been in the news because its tiny elementary school was shuffling to include the children of second-home owners while maintaining social distancing. All over the area, private schools were increasing enrollment and public schools were scrambling to make room at a time when space was sorely needed. Even Avenues, a globally branded school with a branch in Manhattan, opened an East Hampton annex.

But if scoring a school slot had become a new Hamptons challenge, scoring a table at a hot new restaurant remained as it had always been. I nailed a reservation at Carbone, the red-sauce Italian Greenwich Village hot spot that had expanded into a pop-up space in the old Polish social hall in Southampton.


From left: Carbone restaurant, in Southampton; guest bicycles at the Roundtree hotel, in Amagansett. Amanda Villarosa

With my pal Irene Albright, the stylist and owner of New York’s Albright Fashion Library, I sat down next to some privet with a parking lot on the other side. She assessed the fashionable diners around us, looking smug while sampling the well-reviewed cuisine. “I had to hear about these meatballs all summer,” she said. “People have been talking about this place more than the traffic.” We agreed the food was superb.

On the first day of the academic year (although many schools had postponed), every window of the old red-brick Amagansett elementary school was wide open. It was quiet outside, except for the two young parents at the front door, talking to the principal about enrolling their eight-year-old daughter. After dropping that their neighbor was on the school board, they peppered her with so many health questions that she fled and sent out the school nurse. While some private schools were testing for COVID-19, this public school was not.

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“It’s not that we don’t trust you,” said the mother, shifting in her Jack Rogers gold sandals and off-white dress that seemed better suited for a cocktail party. “We’re just concerned.”

The nurse kept smiling. Then she said, “We’re just doing the best we can.”

It’s a statement that applies to everyone pitching in to make a strange and extended season as good as it can be, and that includes Christie Brinkley. In March, the longtime local sweetheart rented a tractor and started cultivating the hillside of her rural property near Sag Harbor. On my last stop in the Hamptons, I found her in what she calls her victory garden, where she has been growing enough tomatoes, peppers, squash, beans, and zucchini to supply her family (all three kids moved in with her) and two local food pantries. In form-fitting overalls and a billowing white blouse, she was cooing at her young chickens, who were gathering around her like paparazzi. She talked about plans for expanding her yard for more farming and dropping off not just her vegetables and flowers but also fresh-laid eggs to the pantries. When she opened the doors to the henhouse, she clucked with delight. “Wow, they laid nine today,” she said.

While she misses the Tribeca pied-àterre she gave up, she knows how lucky she is to be able to have a safe home to enjoy and the time to witness the change of seasons.

Brinkley was heartsick and scared during the worst of the pandemic. “But you have to keep living and pitch in and do what you can to help your neighbors,” she said as she inspected some purple asters and cosmos with chipped red nails that matched her checked mask.

She smiled at her chickens, then sang to them, “Chickadee-doo-da, chickadee-yay.”

It was, in fact, a wonderful day.