The Hamptons off-season is a magical time for locals. From empty beaches to restaurant deals and nature doing its thing with an almost biblical beauty you have to see to believe. Snowfall (if it ever happens again) transforms parts of every hamlet into a Norman Rockwell painting. In the fall, gigantic pumpkin patches harkens pastoral Charlie Brown specials. The pop of autumn leaves rival our mind-blowing pink, red, and orange sunsets. We are reminded of how beautiful this region is. So we asked a few East End agents what they love, and how they enjoy their time, this time of year.
Bonita DeWolf, The Corcoran Group
In September, I had a college roommate visit from Hawaii and she wanted to see the sun rise over the Atlantic Ocean. I declined to go with her at the time but she sent me these amazing photos that made me very curious. Since the sun rises later in the winter, I have made it a point to get up before dawn a few times and take my two dogs to Main Beach to watch the sunrise. They get so excited because it’s so early. There seems to be several people who do this regularly and it’s an inspiring way to start the day. During the colder months it is also appealing to do yoga in a warm or hot room. Align Yoga is a new studio in Amagansett and the owner, Alison Burke, has special infrared lights that are especially healing.
I also recently went to the Parrish Art Museum with my daughter and other visiting family. It was great to see their reactions and they all found it to be a very special place. Afterwards, we went to brunch at Pierre’s and it was fun with great food – as always.
Deborah Srb, Sotheby’s International Realty
Off-season used to be a challenging time out here with everyone always asking “What do you do during the winter? Isn’t it boring?” to which after 30 years in the Hamptons I can respond with an easy answer … anything that you would do anywhere else when the weather changes, except the volume of people diminish. You don’t put on a bathing suit to go to the beach and swim — though there are a few daredevils who do. I find the beach is even more exhilarating and dramatic now. It’s quieter, but there are people walking their dogs and taking in the beauty of dramatic sunsets. Almost all restaurants are still open, but now you can get a table when you want. The Parrish Museum and Southampton Arts Center offer exciting exhibits year-round, the Sag Harbor Cinema is up and running, walking trails are everywhere for the outdoor enthusiast, and there’s even an ice skating rink in Southampton and an NHL regulation-sized ice rink at Buckskill Winter Club. Since the summers are so hectic, I actually love the off-season for re-setting and getting cozy in front of the fireplace. And if I need a little mid-winter break from here, a quick visit to the Bahamas where my dad lives or a ski weekend in Aspen or Montana where my mom lives is always a lucky option I can indulge in.
Matthew Breitenbach, Breitenbach Advisory Team, Compass
The Hamptons is a special place in all seasons. A consistent in all the seasons is just the feel of the entire area — the farms, villages, etc. It is a special place. It is the new Greenwich, but cooler. It’s not about visitors anymore. The Hamptons has become a country town, not just a resort town. And after Covid, it’s a country town that also has new local affluent year round residents that call it home.
Peter McCracken, The Corcoran Group
I believe the off-season is the best part of living on the East End. For me, living on Shelter Island with its remoteness, going out to a late lunch in Sag Harbor, or any of the other wonderful restaurants in the Hamptons, is a great way to enjoy the quietness that the off season brings. Walking through Mashomack Preserve is a wonderful way to relax on a sunny brisk day. If the weather is looking good for the weekend, people still come out to the Hamptons and Shelter Island to get away from the city, especially on the holiday weekends.
Judi Desiderio, Town & Country Real Estate
Go out to dinner! This time of year, there’s no waiting and everyone inside knows us. It’s like “Cheers.” We do travel further for dinners to Westhampton Beach or the North Fork and Shelter Island. We also have the opportunity to gather more with family and friends.
Kevin Flaherty, Compass
The Hamptons has something to offer during every season. In the winter you can find the restaurants that you normally need a reservation for weeks in advance nearly empty. Sag Harbor puts on a winter event called HarborFrost that my family looks forward to every year. The roads are filled with ice sculptures, restaurants are bustling, and the afternoon is topped off with fireworks over the Long Wharf. Between our annual beach bonfire on Christmas eve, trail walking, and ice skating the desolate ponds hidden back in the woods, there is almost always something to do. It may seem quiet but if you’re with good company, dress warmly, and get outside there is almost always something to do.
Angela Boyer-Stump, Sotheby’s International Real Estate
A heavy winter coat and a warm hat are needed but a crisp walk on our gorgeous ocean beaches is the perfect way to start the day! The off-season evening light as the sun sets over the bay is mesmerizing, and the purple, orange, and fire red reflections on the water can only be experienced this time of the year. The social events keep you busy with fun outings like the Hamptons Film Festival, Pumpkintown, Winterfest, Sag Harbor Harborfest, Parrish Art Museum events, and live music at the renowned Stephen Talkhouse. Dining continues through the winter months as many of our best restaurants remain open. Pickleball and indoor tennis have become increasingly more popular and although I am not an ice skater, many enjoy the rinks in Southampton and East Hampton. When you’re done with your workout, indulge yourself at the Topping Rose Spa or Gurney’s!
Dana Trotter, Sotheby’s International Realty
I’m a year round equestrian so I love riding through the fields this time of year when I have a little more time and am not training for horse shows in the ring. I can go to the indoor ring if the weather turns. On mild winter days, we take the dogs to Sagg Main Beach or run to the local Greenbelt trails. Platform tennis, indoor tennis, golf, and movies are good diversions. The relaxed dining and shopping scene is another perk of quiet winters out east.
Patrick McLaughlin, Douglas Elliman
I still visit the beach on a daily basis in the off-season. Because of the position of the sun we actually get sunsets on the water/ocean. You don’t see that in the summer and it’s still one of the best kept secrets of East End living.
Another plus is just hunkering down with a great fire and small group of friends for dinner. In the summer the events, parties, and benefits have most residents running around and filling up their weekends way in advance. Right now a casual get-together is much easier for most and truly one of the highlights of the off-season.
Jake Sinacori, Nest Seekers International
I would say the off-season is a great opportunity to enjoy peace and quiet before the controlled chaos of the summer season. I love to go for walks and runs on not-so-chilly days on the beach in Southampton, take drives out to Montauk (nothing beats the views of the ocean from Old Montauk Highway), get lunch in Sag Harbor, and take the ferry from North Haven and sight see.
