Exploring Montauk in the Winter

Stretching 118 miles from one end to the other, Long Island lives up to its name. But those who choose to make the trek out to the island’s easternmost point are surely rewarded, and that prize is Montauk. Although known as a summertime hot spot, noted for its remarkable beaches, fishing and exciting nightlife, a getaway to Montauk in the winter could prove to be just as memorable, if not more.

As the surf shops and beachside bars close their doors and the crowds go flip-flopping back home, the East Hampton hamlet becomes a beach resort in hibernation, transformed into a sleepy nautical town almost overnight. Suddenly Montauk is quieter – less “Hamptons” and more obtainable.

Take a trip to The End this winter season, where you can bundle up for a stroll along some of Long Island’s best beaches, eat local seafood, indulge in relaxing spa treatments, and when the day is over, cozy up by the fireplace at a top hotel (while enjoying off-season rates).

From what to do to where to say and eat, this is your guide to Montauk in the winter.

Getting There

Driving is the most direct route. Best of all, when visiting Montauk in the winter you’ll avoid the dreaded Hamptons traffic that everyone groans about during peak summer months. Need a ride? Use your AAA membership to get a discount on Hertz car rentals.

If you prefer someone else do the driving, reserve your spot on the Hampton Jitney, which departs from several locations in New York City to the east end of Long Island and Montauk year-round. You could also take the LIRR.

Montauk Hotels Open in Winter: Our Top Picks

Montauk Manor

Set on a hilltop overlooking Gardiner’s Bay and Block Island Sound, there is no shortage of spectacular views at this English Tudor-style condominium resort hotel. Room and suite accommodations are available, as well as amenities including an indoor pool, private health club and spa. But after a day of exploring the area, there’s no better place to warm up than by the fireplace in the Manor’s elegant grand lobby. Reserve your spot for the Murder Mystery Weekend, which happens every year in Montauk in winter.

Born Free Suites By The Sea

Experience the Hamptons comfortably, at Dune Resorts’ Born Free Suites by the Sea, where the majority of rooms come with full kitchens. Search for shells along the beach, located just feet away, or walk into town to experience the lull of Montauk in the winter. Also operated year-round in nearby Amagansett are Dune Resorts’ nearby properties Windward Shores and Sea Crest Resort.

Gurney’s Montauk Resort & Seawater Spa

A blend of modern sophistication and beachside cool, Gurney’s is Montauk as you imagine it. Many of the rooms, suites and cottages have sweeping ocean views, which you can enjoy from your private veranda. For the ultimate in relaxation, enjoy marine-enhanced treatments at the seawater spa, featuring an Olympic-size seawater pool with warm, filtered water pumped in from offshore. A good meal is never too far off at one of resort’s several eateries.

FIND AND BOOK A HOTEL IN MONTAUK

Montauk Things to Do

Montauk Point Lighthouse

Take a trip to the famous Montauk Point Lighthouse. The working lighthouse is the oldest in New York State and a National Historic Landmark. Walk the grounds, tour the museum and shop in the gift shop. The lighthouse closes for the season at the end of November but the views from Turtle Hill at ground level are equally stunning.

Montauk Point State Park

Montauk Point State Park is the end of The End, affording picturesque ocean views of where the Atlantic meets Block Island Sound. Walk the beach or hike the nature trails (bring a canine companion along if you wish – leashed dogs are allowed), or cross-county ski when it’s snowy. Hunting and fishing are available when in season and with permits. And die-hard surfers can hit the waves all winter long.

Seal Watching 

Montauk in winter is also the prime place and time for seal watching; search on your own or go on a seal walk, led by state park naturalists to top observation areas throughout the winter. Find more top seal watching spots on Long Island.

Second House Museum

Built in 1797, Second House is the oldest building still standing in Montauk. It is one of the original three residences constructed on the eastern tip of Long Island after the lighthouse keeper’s quarters, made to house cattle and sheep shepherds when Montauk was pastureland. The museum, operated by the Montauk Historical Society, provides a look back into the area’s past.

 

View this post on Instagram

 

A post shared by Montauk Brewing Co. (@montaukbrewco) on Oct 19, 2019 at 8:41am PDT

Wine and Beer Tasting

The North Fork of Long Island gets all the glory for its extensive wine country but the South Fork boasts quite a few great wineries as well. On the drive up or on your way back home, stop and relax with a tasting at Duck Walk Vineyards Southampton, Wölffer Estate or Channing Daughters.

For a tasting experience right in Montauk, visit the laid-back Montauk Brewing Company to sample its handcrafted beers.

 

View this post on Instagram

 

A post shared by Montauk Bake Shoppe (@mtkbakeshoppe) on Apr 30, 2019 at 7:18am PDT

Restaurants in Montauk

Here are a few more places to get a taste of Montauk in the winter.

Montauk Bake Shoppe: Order a few goodies to take back home or bring to your hotel. All are baked fresh on-site. Don’t leave without trying a jelly croissant (you can thank us later).

Surfside Inn: Accompanied by a year-round country inn, this homey restaurant fittingly serves a menu of fresh seafood and comfort foods for lunch and dinner.

John’s Pancake House: A favorite of locals and tourists alike. Though always busy, off-season you won’t have to wait as long for a table.

Candied Anchor: Grab a bag of sweets for your travels from this cute little gourmet candy shop.

Harvest on Fort Pond: Enjoy the sunset on Fort Pond from your table accompanied by family-style Italian cuisine inspired by Montauk seafood. In the warmer months, chefs use ingredients from the on-site garden.

Have you ever been to Montauk in the winter? Tell us in the comments. 

Plan a Montauk getaway with AAA Travel.