Stretching 118 miles from one end to the other, Long Island sure 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.
Hit the road on one of these amazing routes to get a real feel for all America has to offer.
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.
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
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. The on-site restaurant La Fine is a cozy spot to indulge in family-style Italian dining. 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 and free Wi-Fi. 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.
Driftwood Resort on the Ocean
No matter the season, the private beach at the year-round Driftwood Resort is always inviting. This casual, family-friendly retreat offers one-bedroom suites and studios, many with full kitchens or kitchenettes, and some that include private balconies to take in the view.
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 from LDV Hospitality.
Burcliffe by the Sea
Perfect for when you just need to get away, this quiet inn can be your home away from home. One and two bedroom cottages include fireplaces, kitchens and individual patios. And it’s just a short walk from the shore.
Montauk things to do
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 gets illuminated in Christmas lights for the holiday season before closing for the season at the end of November. But the views from Turtle Hill at ground level are equally stunning.
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.
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.
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.
Wine & 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.
Restaurants in Montauk
In addition to the hotel restaurants mentioned above, 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.
East by Northeast: From the same owners as Harvest on Fort Pond and located just a few minutes away, East by Northeast offers the same great view but with gourmet Pan-Asian cuisine. It connects to the Stone Lion Inn, which is open year-round and features waterfront suites.
Have you ever been to Montauk in the winter? Tell us in the comments.
This post was first published in 2018 and has since been updated.