The Hamptons — Southampton, to Be Specific — in Winter

On my first night in Southampton, New York, I made a critical error: I referred to the village as “The Hamptons.”

“We are Southampton,” a local politely informed me.

This kind of interaction with a Southamptoner is exactly why visiting the village in the “off season” — basically any time before Memorial Day or after early September — is such fun.

Some wouldn’t be caught dead in this chic destination this time of year, but why not? You have the whole place to yourself and you get to experience the villagers, that is, the people who live there year-round, not the tourist throng that descends on the area every summer.

Southampton’s “close-knit” spirit is what drew Georgetowners Bruce and Marjie Calvert to buy their weekend place there. “We enjoy the beach and the fishing,” says Bruce, adding that his house is always chock-full of guests, who join in the local pastimes.

If you aren’t lucky enough to stay at Chez Calvert, here’s how to enjoy Southampton this winter in style.

First, grab the Hampton Jitney, which runs year-round from Manhattan at an affordable fare.  

From your bus station upon arrival, you’re only a short Uber ride from the newly opened Maison Vivienne, right on Main Street. I had a chance to spend a couple nights in late October at this 17th-century Dutch Colonial and was charmed by its contrasts: portraits of Brigitte Bardot and girls in go-go boots hover over homely fireplaces. The décor, by Paris K Studio, may be sleek and modern, but the hospitality is old-fashioned.

There are only a handful of rooms at Maison Vivienne, so you get the intimacy of a bed-and-breakfast with the service (and bar) of a large hotel. Chef de cuisine Christian Souvenir brings his New Orleans warmth tableside, chatting up guests about his entrees, like his organic chicken with red beans and rice risotto. Top that off with a decadent dessert or a drink from the hotel’s prodigious wine cellar by the fire.

For a true Southampton breakfast or snack, go across the street to Catena’s Market, which has been run by the same family for generations. The owners will provide you with all the local gossip and point you in the right direction to see the best Southampton haunts.

I headed down Main Street to check out one of the oldest churches in the country, First Presbyterian of Southampton, which is marking its 375th anniversary.

You’ll also want to see the Southampton History Museum, organized in 1898. It contains artifacts of the city’s proud heritage, which dates back to New York’s founding in the 1600s. Currently, the museum has an exhibition of photographs taken between 1892 and 1940, depicting landmarks and telling the stories of the area’s families.

Keep walking down Main Street, through a never-ending display of spectacular homes and manicured lawns, and you’ll find yourself on the beach, which (during the winter) you’ll experience as peaceful yet bracing. The only beach bum you’ll encounter is probably the local dog out for a brisk walk.

Nature lovers should also take in the serenity of Agawam Lake, especially as the sun is setting. Just look out for a very boisterous phalanx of geese who like to greet visitors there. One of my favorite nature spots in Southampton, highlighted for me by the guys at Catena’s, is Munn Point Preserve. An osprey nest sits not far from the boardwalk. You can birdwatch in this seven-acre salt marsh, where a tidal creek meets the edge of Shinnecock Bay.

On the way back, meander down Meadow Lane for more architectural wonders. There are more deer there than in Rock Creek Park.

Conscience Point, a short Uber ride from Maison Vivienne, is another nature’s paradise, where I found two young men teaching a spaniel to hunt near the shore. There is a large rock with a plaque marking the spot where colonists founded the first English settlement in 1640. The Conscience Point Marina is another great place for a wintry, bundled-up stroll.

The North End Graveyard dates back to the American Revolution and also happens to be the resting place of actor Gary Cooper.

Finish your day with a beer and a burger at Fellingham’s Restaurant and Sports Bar. In its friendly pub atmosphere, you’ll get more local flavor and ideas for your next day’s adventure.

Maison Vivienne in Southampton, New York. Photo by Stephanie Green.

Conscience Point in Southampton, the historic spot where colonists founded the New York settlement in the 1600s. Courtesy Stephanie Green.

First Presbyterian Church of Southampton, celebrating 375 years. Photo by Stephanie Green.

Southampton boasts many nature spots for brisk winter walks. Try a stroll around Agawam Lake. Photo by Stephanie Green.


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