NEW YORK STATE’S SEE-AND-BE-SEEN summer getaway of celebrities from Martha Stewart and Stephen Spielberg to Madonna and Jimmy Fallon, the Hamptons makes a tempting stopover. Stretching east from Manhattan, Long Island ends in upper and lower prongs offering beaches, vistas and vineyards. But it is the South Fork most people mean when they refer to “the Hamptons.” Spanning about 30 miles, it encompasses a half dozen seaside communities — oldmoneyed and gentrified Southampton; Sag Harbor, the hub of actors and writers; East Hampton with its glittery show business scene; more restrained Water Mill; Bridgehampton; and Amagansett. There’s also Sagaponack, which rates as the most expensive zip code in America, and laid-back Montauk, at the far end, a haven for bohemians, fishermen and surfers.
It’s summertime when you’re most apt to encounter Alec Baldwin or Sarah Jessica Parker buying newspapers at CandyKitchen, window shopping at Ralph Lauren, stocking up on crispy mustard-roasted chicken at the Barefoot Contessa or waiting in line for lattes at Starbucks. But Memorial Day to Labor Day the whole region also suffers frequent gridlock with bumper-to-bumper traffic on vital Route 27. The Hamptons in winter is a whole different matter. While you’re less apt to encounter famous faces and some of the attractions close down, in off-season visitors can truly relax, bask in the scenery and score restaurant reservations and discounted hotel rooms. All year-round there’s plenty to do.

East Hampton shopping district © JAMES KIRKIKIS | DREAMSTIME.COM
The No. 1 attraction is the region’s glorious beaches for basking, jogging, strolling, paddle boarding and picnicking. While the daily parking permit fee is $40 at Southampton’s Coopers Beach (and an extra $25 for chair and umbrella), there’s no charge for just walking onto glorious stretches of sand like East Hampton’s Main Beach or Montauk’s marvelous dunes, and some hotels provide dropoff service. Bicycles are another option; most villages have rental shops for pedaling to the nearby stretches of sand where you can easily stash cycles.
Golfing offers another way to take in the scenery. Montauk Downs, Sag Harbor Golf and Poxabogue in Bridgehampton are public courses with spectacular settings. Around a dozen facilities rent tennis courts, even in winter at East Hampton Indoor Tennis. Fitness centers like Soul Cycle and Pilates studios offer spin, exercise and yoga classes year-round. When it’s cold, enjoy pick-up hockey games, skating and ice boating on Mecox Bay.
In a locale with so many illustrious residents, culture lies at the forefront. Authors Jay McInerney and Tom Wolfe may promote their books in library readings or join more than two dozen writers signing their works at East Hampton Library’s annual outdoor Authors Night benefit. Jennifer Lopez, Gwyneth Paltrow, Emily Mortimer, Alessandro Nivola and other actors and directors may host screenings of their movies, and the Hamptons Film Festival takes over local theaters each October. Sag Harbor’s Bay Street Theater hosts Broadway shows and comedy nights.
Fueled by the legacy of former artist-residents Jackson Pollock, Willem de Kooning and Lee Krasner and now augmented by modern painters Eric Fischl, Donald Sultan and April Gornik, the East End provides rich opportunities for art lovers. Local galleries and tents set up for art fairs in July offer revolving exhibits. The rambling Herzog & de Meurondesigned Parrish Art Museum and the stately Southampton Arts Center show exhibits all year. On weekends, Dan Flavin’s fluorescent light creations are displayed in the Art Institute established in a former firehouse.
Founded in the 1640s, the villages tout their histories. The colonial Thomas Halsey Homestead, the 17th-century Pelletreau Silver Shop and the Rogers Mansion list among historic structures comprising the Southampton Historical Museum, which sponsors play readings, lectures and classes. Of its half dozen historic buildings, East Hampton’s 1720 Osborn- Jackson House remains open year-round, and the Society runs a winter lecture series. Sag Harbor’s Whaling & Historical Museum houses the state’s largest collection of whaling equipment, and the stately building fronted by Corinthian columns has been declared a National Treasure. Standing 110 feet tall, the Montauk Lighthouse displays the actual document George Washington signed authorizing its construction.

Cedar Point Lighthouse in East Hampton © SYLVANA REGA | DREAMSTIME.COM
Before its transformation into a resort, the South Fork was agricultural. Most of its onceextensive potato farms have been lost to development, but you’ll still find farmers raising corn, squash, zucchini, sun-ripened tomatoes, flowers and autumn pumpkins — all of which provide traffic-stopping glories of roadside farmers markets. From February through May produce is sold at the enclosed Fair Foods Farmers Market in Sag Harbor.
One enduring local crop is grapes. Notable wineries feature year-round tastings and tours to show off vintages of Merlot, Cabernet, Chardonnay and Pinot Grigio. Reflecting its German heritage, the Wölffer Estate in Sagaponack entertains visitors on a stone terrace or under the high-beamed ceiling within its recently renovated tasting room while local jazz musicians entertain guests nibbling at cheese and charcuterie and sipping reds and whites. Channing Daughters Winery offers artisanal wines from hand-picked grapes which are gently cluster-pressed or footstomped and gravity bottled. Open daily yearround, Channing welcomes drop-ins 11 a.m.–5 p.m. for informative tastings of six different wines each day.

Wölffer Estate’s new tasting room in Sagaponack © BRIDGET ELKIN
Spa seekers can try Gurney’s in Montauk, where a Roman bath, Finnish rock sauna, Russian steam room, Swiss shower and a unique ocean-fed saltwater pool augment healing treatments. Gurney’s also rents oceanfront rooms and, like most accommodations in the region, offers more or less half-price off-season rates and packages. Those who come to shop find Ralph Lauren, Calypso, Madewell and other familiar brands in East Hampton, while the Main Street of every village is lined with charming shops and quirky boutiques.
The Hamptons Info to Go
While the stars fly out by helicopter, most visitors avoid the rural East Hampton Airport. Off season, the 100-mile drive takes an easy two hours from Manhattan, but that can more than double in the throes of summer traffic. The Montauk Branch of the Long Island Railroad schedules two to five trips per day to and from Penn Station. The preferred option is the ultra-efficient coach service of the Hampton Jitney and Luxury Liner that offer WiFi and snacks on board. Their frequency is almost hourly in summer, with pick-up and drop-off at East- and Westside Manhattan locations, plus an airport connection.
Where to Stay in The Hamptons
THE AMERICAN HOTEL Eight shabby-chic double rooms are in demand at Sag Harbor’s vintage 1846 hotel, revamped in the 1970s with sitting rooms, Frette linens and oversized bathrooms, steps away from the popular hangout bar downstairs. 45 Main St., Sag Harbor $$$ ($$$$$ in summer)
MAIDSTONE ARMS Snuggle into “Scandinavian- cozy” European flair in 19 rooms and cottages with Covuchi robes, aromatherapy burners, Malin+Goetz bath products and a hearty buffet served on the ground floor. 207 Main St., East Hampton $$$$ ($$$$$ in summer)
SOUTHAMPTON INN This grand dame hotel offers almost 100 rooms decorated in traditional style with an outdoor pool, tennis court, game room and gym. 91 Hill St., Southampton $$$ ($$$$ in summer)
Restaurants in The Hamptons
NICK AND TONI’S Summer reservations are at a premium at this celebrity favorite where lucky diners enjoying wood-roasted whole fish or crispy duck leg could be seated near Brad Pitt and Jack Nicolson. 136 N. Main St., East Hampton $$$$
PIERRE’S Bouillabaisse, blanquette de veau and other traditional French fare round out the seafood-focused menu, dish of the day and fixed-price menu at this chic and casual café with outdoor summer seating. 2468 Main St., Bridgehampton $$$
TOPPING ROSE HOUSE Enjoy sensible, locally sourced versions of renowned chef Jean- Georges Vongerichten’s sophisticated French cuisine in the elegant, historic dining room. 1 Bridgehampton- Sag Harbor Turnpike, Bridgehampton $$$$
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