In the summer, Long Island’s East End is overcrowded, frenetic, often scary. Highway traffic builds up for miles. Restaurants are filled with welcoming egos and good luck finding parking near the beach.
“I remember growing up there and it was dead in the winter. But now it’s almost like an opportunity to go to the restaurant that I didn’t get to book in the summer at all.”
Lexie Routh resident of Watermill
But there’s another side: a Hamptons that’s peaceful, family-centered, wholesome. It’s the Hamptons of the here and now—and it’s better than ever.
“The number of year-round families there has definitely increased,” said Lexie Routh, a Water Mill resident who grew up in the East End and now splits her time between the city. “After the pandemic, one of my friends, a teacher in Sag Harbor, said class sizes doubled. But in the last year, now that some offices are getting people back to work, it’s gone down a bit.”
This ebb and flow has created a happy medium, with enough full-time employees to support businesses and events throughout the year, but not so much that it feels overwhelmed.
“I think it’s pretty cool,” Routh said. “I remember growing up there and it was dead in the winter. But now it’s almost like an opportunity to go to the restaurant that I didn’t get to book in the summer at all.”
It’s true of all Hamptons hotspots. Wölffer Estate becomes more feasible; you can go inside. Bookings at Tutto il Giorno in Southampton? Easy. Looking for nightlife? There is still a scene in Calissa at Millwater.
Below is a guide, put together by a brain trust of full-time Hamptonites, to the winter wonderland that stretches from Southampton to Montauk.
Where to eat
Off-season, the Hamptons is your pearl oyster, with openings at many of its trendiest establishments. But if you’re after convenience, hit one of the area’s growing year-round restaurants. The East Hampton Grill is an all-season venue for carnivores; as is the French favorite Sant Ambroeus. The 1770 home of executive chef Michael Rozzi is also open.
In Montauk, Scarpetta Beach at Gurney’s Montauk Resort is the premier Italian restaurant every month of the year. And in Amagansett, the beloved Rowdy Hall bistro has found a new year-round home on Main Street.
On Sag Harbor’s Main Street, Lulu’s is serving up warm wood-fired meals all winter long. And nearby, new American seafood spot Bell & Anchor is a waterfront spot that doesn’t mind a little snow on the beach. But what’s a trip to the Hamptons without a lobster? Grab a warm, buttery lunch at Southampton’s Seafood Shack (officially called the Lobster Roll).
No matter which village you choose, you will be spoiled for choice.
Internal information: Don’t forget the local old-school venues that have supported year-round for generations. For example, Shippy’s in Southampton Village is a classic.
What should be done
This weekend, the Parrish Art Museum hosts a holiday market with 20 vendors, art and activities for children.
When you’re done, enjoy a complimentary cocktail benefiting the Southampton Animal Shelter hosted by Little Lucy’s Dog Fashion Boutique. In East Hampton, Guild Hall’s Boots Lamb Education Center hosts free gingerbread cookie decorating with cookie artists from Citarella in December. 16.
The Southampton Wellness Oasis Shou Sugi Ban House is open throughout the winter and even hosts off-season holidays.
In January, they have author and speaker Lydia Fenet for a three-night “Claim Your Confidence” inspirational event (from $5,743).
Meanwhile, Rachel Lozina’s Blue Water Spa in Southampton also stays open – specializing in teen treatments and mother-daughter days.
Bundle up and head to LongHouse Reserve, 16 acres of art and gardens in East Hampton, for Sunday meditation sessions.
For a different kind of relaxation — the cozy, puffy kind — swing by the Thursday jazz nights at Claude’s, the Southampton Inn’s signature restaurant. All cats dig it.
Internal information: Beware of the “trade parade”. From around 4pm to 6pm, roads may be blocked by commuters.
Where to stay
The absolute best part of heading east in the off-season is the hotel rates, which drop like cleavage at the Surf Lodge. For example, rates at the tony Topping Rose House in Bridgehampton, with its eponymous restaurant Jean-Georges, drop to $395 a night in December (you’ll pay $3,885 for the nightly peak season).
The Roundtree in Amagansett offers 20% off regular room rates from December through the end of March. Baker House 1650, the East End’s most luxurious bed and breakfast, offers two winter weekday nights — with spa treatment — for $688.
Sag Harbor hotspot Baron’s Cove closes for January, but you can get rooms now for as little as $161 a night or $176 in February. Gurney’s Montauk Resort goes for $250 a night in February.
Internal information: Book midweek when staff have the time and energy to go the extra mile.
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Image Source : nypost.com