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In the summertime, Long Island’s East End is overly full, frenetic, often formidable. The traffic on the expressway backs up for miles. The restaurants are rife with expectant egos, and good luck finding parking near the beach.
“I remember growing up out there and it was dead in the winter. But now it’s almost like an opportunity to go to the restaurant that I couldn’t get a reservation at all summer.”Water Mill resident Lexie Routh
But there is flip side: a Hamptons that is peaceful, family-focused, healthful. It’s the Hamptons of right here and now — and it’s better than it’s ever been.
“The number of year-round families out there has definitely grown,” said Lexie Routh, a Water Mill resident who grew up on the East End and now splits her time between the city. “After the pandemic, one of my friends, a teacher in Sag Harbor, said that class sizes doubled. But in the last year, now that some offices are making people come back to work, it’s declined a little bit.”
That ebb and flow has created a happy medium, with enough full-timers to support year-round businesses and events, but not so many that it feels overladen.
“I think it’s really nice,” said Routh. “I remember growing up out there and it was dead in the winter. But now it’s almost like an opportunity to go to the restaurant that I couldn’t get a reservation at all summer.”
It’s true of all of the Hamptons hot spots. Wölffer Estate becomes more feasible; you can walk in. Reservations at Tutto il Giorno in Southampton? Easy. Looking for nightlife? There’s still a scene at Calissa in Water Mill.
Below is a guide, gathered from a brain trust of fulltime Hamptonites, to the winter wonderland that stretches from Southampton to Montauk.
Where to eat
Off-season, the Hamptons is your oyster, with openings at many of its toniest establishments. But if you’re after ease, frequent one of the area’s growing number of year-round restaurants. The East Hampton Grill is an all-seasons spot for carnivores; as is Frenchie favorite Sant Ambroeus. Executive chef Michael Rozzi’s 1770 House is also open.
Out in Montauk, Scarpetta Beach at Gurney’s Montauk Resort is the premier Italian eatery every month of the year. And in Amagansett, beloved bistro Rowdy Hall has found a new year-round home on Main Street.
Over on Sag Harbor’s Main Street, Lulu is serving warming wood-fired meals all winter. And nearby, new American seafood spot Bell & Anchor is a waterfront venue that doesn’t mind a little snow on the beach. But what’s a trip to the Hamptons without a lobster roll? Get one warm and buttered at Southampton seafood shack Lunch (officially dubbed Lobster Roll).
No matter which village you choose, you’ll be spoiled for choice.
Insider info: Don’t forget the old-school local spots that have supported year-rounders for generations. For instance, Shippy’s in Southampton village is classic.
What to do
This weekend, the Parrish Art Museum hosts a holiday market with 20 vendors, art and activities for the kiddos.
When you’re done, enjoy a complimentary cocktail at a benefit for the Southampton Animal Shelter hosted by Little Lucy’s canine couture boutique. In East Hampton, Guild Hall’s Boots Lamb Education Center is hosting free gingerbread cookie decorating with cookie artists from Citarella on Dec. 16.
Southampton wellness oasis Shou Sugi Ban House is open all winter and is even hosting off-season retreats.
In January, they have author and speaker Lydia Fenet for an inspirational “Claim Your Confidence” three-night event (from $5,743).
Meanwhile, Rachel Lozina’s Blue Water Spa in Southampton also stays open — it’s specializing in teen treatments and mother-daughter days.
Bundle up and head to the LongHouse Reserve, with 16 acres of art and gardens in East Hampton, for Sunday meditation sessions.
For a different type of relaxation — the cozy, boozy kind — swing into the Thursday jazz nights at Claude’s, the Southampton Inn’s signature restaurant. All the cats dig it.
Insider info: Beware the “trade parade.” From about 4 to 6 p.m., roads can clog with commuters.
Where to stay
The absolute best part of heading east off-season is the hotel rates, which plummet like the necklines at Surf Lodge. For instance, rates at tony Topping Rose House in Bridgehampton, with its eponymous Jean-Georges restaurant, drop to as little as $395 a night in December (you’ll be paying $3,885 a night peak season).
The Roundtree in Amagansett offers 20% off its regular room rates from December through the end of March. Baker House 1650, the East End’s most luxurious bed-and-breakfast, is offering two nights during winter weekdays — with spa treatment — for $688.
Sag Harbor hot spot Baron’s Cove closes for January, but you can pick up rooms right now for as little as $161 a night or $176 in February. Gurney’s Montauk Resort goes for as little as $250 a night in February.
Insider info: Book midweek when staff have the time and energy to go the extra mile.
