Known for its serene setting and sandy beaches, the Hamptons is a favorite summer destination for New Yorkers looking to escape the city. But maybe we should start thinking about it as a year-round destination getaway. It may be too cool to take a dip in the ocean, but the Hamptons still contain world-class vineyards, shopping, art, dining, and seasonal events in the cooler months, too. 

For a guide to the perfect Hamptons off-season trip, read on!

Go Wine Tasting through the Vineyards

The beloved stretch of Long Island is home to over 60 vineyards and wineries, with particular renown for superb reds, such as the classic Bordeaux, Cab Savs, and Merlot. Here are a few recommendations to get you started.

Bedell Cellars
Bedell Cellars is a pioneering, family-owned winery committed to sustainable farming. Sample hand-crafted small batch wines, including carbonic Malbec, White Cabernet Franc, and a famous Malbec red, while taking in sweeping views of the vineyards and gardens. There’s also a menu featuring artisan salumi, cheese, and rustic bakery bites available with wine tasting. And don't miss weekly live music in the Corey Creek Tap Room.

Hours: Open 11-7 PM Sunday—Thursday, 11-8 PM Friday and Saturday, no reservations.
Where: 36225 Main Rd, Cutchogue, NY 11935

Macari Vineyards
A gorgeous large deck overlooks the 500 family-owned acre waterfront vineyard and farm in Mattituck. There are a variety of guided tasting experiences for small and large groups, and tasting flights and glasses are available by reservation.

Hours: Open Monday—Thursday 9 AM—5 PM, Fri—Sun 11 AM—6 PM
Where: 150 Bergen Ave, Mattituck, NY 11952

Pindar Vineyards
With a tasting room open seven days a week, live music on Saturdays and Sundays, and an award-winning signature white blend made of Honeysuckle, citrus blossom, and notes of Mango and tropical fruits, Pindar is a must. Indoor and outdoor tables are first come, first serve, but guests are welcome to bring their own blankets and beach chairs.

Hours: Open daily, 11 AM—5:30 for tastings and 6 PM for sales. 
Where: 37645 Main Rd (Rt 25), Peconic, NY

Croteaux Vineyards: Corteaux Vineyards is one of America’s only vineyards to produce strictly Rose wines. Open seasonally until late November, the gorgeous first come first serve tasting garden is filled with pumpkins and gourds in the fall, along with heaters and warm blankets. They also offer a cozy Croteaux tasting room to sip in. 

Hours: Daily, 12—6 PM, no reservations.
Where: 1450 South Harbor Road, Southold, NY 11971

Wolffer Estate: Not only does the Wolffer estate span approximately 175 acres including the acclaimed 55-acre sustainably farmed vineyard located in Sagaponack, the family also owns acres on Long Island, Argentina, Spain, and France. Committed to producing premium, distinctive wines, ciders, and spirits, the estate has a wide variety of spirits to taste and choose from.

Where: 139 Sagg Road, Sagaponack, NY 11962
Hours: Winery open daily, Sunday—Thursday 11 AM—6 PM; Friday—Saturday, 11 AM — 8 PM

Hank’s Pumpkintown

Pumpkin picking, apple picking, corn maze wandering, and more are all in season and open till Oct 31st at Hanks Pumpkintown. There’s also a range of sweet-tooth treats from freshly baked pies, candy apples, and ice cream, to cider donuts, cider slushies and soft pretzels. And for the adults, a hard cider tasting room awaits.

Where: 240 Montauk Hwy, Water Mill, NY 11976
For more information Hank’s Pumpkintown.

East Hampton Village Fall Festival | Oct 28th—30th

If you're in the Hamptons for Halloween, don’t miss three days of over 50 local business goods, live music, community art projects, and kid zones for the little ones at the East Hampton Fall Fest. Expect costumes, pumpkin carving contests, and tons of seasonal food and drinks to enjoy.

Where: 67 Newtown Lane East Hampton NY 11937                        
For more information East Hampton Fall Fest.

Stay at The Baker House 1650

Nestled in the beautiful, historic Village of East Hampton, guests are greeted by vine-covered walls, a lush English garden, and the artfully designed pool of B&B dreams. Days here start with a garden-side breakfast made from local and organic ingredients, a dip in the sparkling infinity-edge pool (preferable with a glass of small-batch bourbon or champagne in hand), and a trip to the guest-only Baker Spa sauna. In other words, pure bliss.

Where: 181 Main St, East Hampton, NY 11937
For more information on the Baker House 1650.

Sag Harbor Cinema

Take dinner and a movie into the modern age with Sag Harbor Cinema, a brand-new triplex movie theater in the village of Sag Harbor. The film selection is meant to honor the past and present, so you’ll find both classic films and new releases on the calendar. Just make sure to start at the Cinema’s third-floor bar and rooftop terrace, The Green Room, open only to cinema guests and members.

Where: 90 Main St, PO Box 152 Sag Harbor
For more information Sag Harbor Cinema

Highway Restaurant and Bar

Loved for its well-crafted New American menu filled with inventive appetizers and unique nightly specials, Highway Restaurant and Bar is the place to dine in East Hampton. Notably, “Thai Nights” have returned, serving three-course authentic Thai meals for $35 every first Thursday of the month. Saturdays will also feature live sushi bar service, and on Sundays, you can grab wood-fired pizzas from a truck from 5–9 PM. Mangia! 

Where: 290 Montauk Hwy, East Hampton, NY 11937
For more information on Highway.

Westhampton Beach Performing Arts Center

There are more shows to enjoy in New York than just Broadway! The Westhampton Beach Performing Arts Center is a year-round, community-based performing arts venue that puts on world-class performances from ballet and music to comedy and cinema.

Where: 76 Main St, Westhampton Beach, NY, United States, 11978
For more information on Westhampton Beach Performing Arts Center.

Shop the Boutique Stores

Boutiques, luxury stores, and vintage goods all abound in the Hamptons. Whether you’re buying art at Eric Firestone Gallery in East Hampton, leather goods, jewelry, and clothing from upscale stores in Southampton, or browsing the trendy shops of Montauk (Gucci x Melet Mercantile, LoveShackFancy), you’re certain to find a gem.

For a full day's worth of retail therapy, try Main Street Southampton. Along with some amazing restaurants, make sure to check out Aerin for jewelry and Homenature for furniture.

Where: Main St, Southampton, NY 11968
For more information on Southampton Downtown.

Shou Sugi Ban House

Calm your mind from the noise of the city, and enjoy a restorative afternoon at Shou Sugi Ban. Book a range of spa treatments from hydrotherapy and sauna treatments to body massages and facials. Also available are sessions in healing arts, fitness, and nutrition, as well as culinary offerings for a truly nourishing experience.

Where: 337 Montauk Hwy, Water Mill, NY 11976
For more information on Shou Sugi Ban House.