An Off-Season Guide to the Hamptons & Montauk

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Advisor - Jacqueline Puzo
Curated By

Jacqueline Puzo

  • New York

  • Food & Wine

  • Luxury Travel

  • Wellness Travel

  • Beach Town

  • Foodie

  • Shopping

A lighthouse during daytime.
Curator’s statement

When I think of the Hamptons, I think of pristine beaches, stunning homes, wonderful restaurants, luxurious spas, great shopping, delicious farm stands, wineries and peaceful walks. Having lived there year-round, I came to appreciate the charm of the off-season. It's more laid-back and quiet, but there's still plenty to do – you can easily get into the best restaurants, enjoy the beaches without a permit, and find more affordable hotel stays.

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Things to do in Hamptons

A dune on a sunny day.
  • Beaches/Hikes/Parks: Hike the Walking Dunes at Hither Hills State Park in Montauk Easy hike known for 80-foot sand dunes that move over three and a half inches a year. Take the short loop ending on the beach. Cooler months are best for fewer bugs and easier parking (although sparse). Dress warm!

  • See the Montauk Point Lighthouse: Located on the very tip of Long Island, enjoy 360 degree views from the first lighthouse built in New York and fourth oldest in the nation.

  • Watch the waves crash at Coopers Beach in Southampton: Named one of the best beaches in America. Drive right up to the beach’s edge to watch the waves crash or take a peaceful stroll along the shore to admire the estates, including the iconic ‘Something’s Gotta Give’ house.

  • Birdwatch at the Elizabeth A. Morton Wildlife Refuge in Sag Harbor: A 187-acre sanctuary that is a haven for native birds and wildlife including turtles, frogs, songbirds and osprey. Take the Wild Birds Nature Trail followed by a leisurely walk along the scenic beach of Jessup's Neck Peninsula.

  • See Sunset at Long Beach in Sag Harbor: A beautiful, long stretch of rocky bay beach on the Peconic. In warmer weather, get a lobster roll at Cappelletti and eat it on the beach watching the sun go down over the tranquil waters of the Peconic Bay.

Spas:

  • Shou Sugi Ban House, Water Mill - Indulge in the epitome of tranquility and luxury at this serene spa and wellness retreat. Enjoy a spa treatment and savor a nourishing meal featuring organic produce grown on the east end. Go for the day or stay the night.

  • The Seawater Spa at Gurney’s, Montauk - Immerse yourself in the tranquility of this recently renovated oasis, crafted with the creators of AIRE Ancient Baths. Unwind in the rejuvenating bathhouse experience and treatment suites with scenic views of the Atlantic Ocean.


Other

  • Longhouse Reserve, East Hampton - Discover the 16-acre estate of world-renowned textile designer, Jack Lenor Larson. Tour in the Spring with a master horticulturist to see almost a million daffodils, along with cherry trees, tulips, magnolias and art installations throughout the gardens.

  • Clubhouse, East Hampton - A fun destination for kids and adults alike offering bowling, mini golf and arcade games. Grab a meal and watch the game in the on-site restaurant and enjoy live entertainment in the evenings.

  • Amber Waves, Amagansett - explore this community farm that spans over 30 acres and grows over 60 different crops. Take a self-guided tour of the farm or grab a bite in the Kitchen & Market.

Day Trips

  • Shelter Island - Take the boat from North Haven to this tiny island in between the North and South fork. It’s quiet in the off-season but take the chance to explore. Go to Shelter Island Craft Brewing, have lunch at the Flying Goat restaurant and take a walk in the Mashomack Preserve in the afternoon.

  • North Fork - Head to the other side of the Peconic where you’ll find over 60 vineyards, breweries and craft distilleries. Check out Macari, Sparkling Pointe and Kontokosta wineries or spend the day exploring Greenport.

Places to eat & drink in Hamptons

Vineyard on a sunny day.

Wineries:

  • Wolffer Estate Vineyard, Sagaponack: Delight in the picturesque grandeur of the estate and its stunning grounds. Indulge in a wine and cheese pairing in the Tasting Room or go for Candlelight Fridays. For a more relaxed setting, visit the Farm Stand.

  • Duckwalk Vineyards, Watermill: Come here for a more relaxed and casual experience. Bring your own food and listen to live music on the weekends. The perfect place to go after Hank’s Pumpkintown in the Fall.

  • Channing Daughters Winery, Bridgehampton: Offers a more low key, yet sophisticated atmosphere. Enjoy a tasting flight while watching the sunset over the scenic vineyards.

Restaurants:

Dinner

  • The Bell & Anchor, Sag Harbor: You might think it’s a kitchen store at first, but the incredible food makes up for its unassuming exterior. When we saw Michelin star chef, Eric Ripert, dining there we knew it was top-notch. Everything is delicious but my favorites include the bouillabaisse, lobster and almond cake.

  • T Bar, Southampton: Named after its proximity to the train, expect simple yet delicious food in a relaxed, sophisticated ambiance. Menu highlights include the crispy sushi, thin crust pizza, chopped salad and more.

  • East Hampton Grill, East Hampton: A mainstay American grill known for its good food, drinks, and service. With a dark wood interior, it exudes a cozy and warm vibe, especially during cooler weather.

  • Shippys, Southampton: One of the oldest restaurants in town, Shippys harks back to some of the early visitors to Southampton from NYC and their German roots. Highlight of the menu has to be the Schnitzel but the burgers and wings are good too.

  • Jean-Georges at Topping Rose House, Bridgehampton: Perfect for a special occasion dinner in a gorgeous 19th mansion turned luxury hotel. The crispy tuna sushi is a must!

  • Baron’s Cove, Sag Harbor: Cozy up in front of one of the fireplaces for dinner or drinks and savor the ambiance at this charming harbor-side hotel.

  • Ciitanuova, East Hampton: Casual, contemporary Italian. Great place to grab a seat at the bar or a table in the garden when the sun is shining.

Lunch

  • Bostwick’s Chowder House, East Hampton: Get a warm bowl of chowder and a delicious lobster roll at this casual hotspot. Arrive when it opens for lunch to avoid lengthy waits. Closed Dec-Mar.

  • Fellinghams, Southampton: Once voted best bar in the US by Esquire, Fellinghams draws a diverse crowd. Grab a cold beer at the bar or get a table for bar fare: burgers, hot dogs and chili.

  • Pierre’s, Bridgehampton: A slice of St. Tropez and St. Barts in the Hamptons. Get the tart flambé, steak tartare and great French wine selection.

  • Sag Pizza, Sag Harbor: perfect spot for families with great pizza and dipping sauces.

Breakfast & Brunch

  • American Hotel, Sag Harbor - Brunch: A charming, historic hotel that serves a delicious brunch in an elegant , sophisticated ambiance.

  • Tates, Southampton: A must-visit when in the Hamptons known for their crispy, thin chocolate chip cookies sold nationwide. They also offer a wide selection of baked goods, perfect for breakfast on the go.

  • Grindstone Coffee & Donuts, Sag Harbor: decadent donut spot with delicious seasonal donuts and breakfast sandwiches.

  • Sip & Soda: Old school luncheonette with bacon and egg diner classics. Or go for lunch and have the burger or a grilled cheese washed down with their famous lime Rickey.

Advisor - Jacqueline Puzo

Travel Advisor

Jacqueline Puzo

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For more travel tips, check out Fora Advisor Brittani Friedland’s guide, Where to Eat, Drink and Stay in the Hamptons. This guide is part of our ongoing series on travel to New York.