48 Hours in Montauk

Here's how to spend a chill winter weekend in East Hampton.

Montauk in the winter is nearly a different town altogether than it is during the bustling summer months. Few people think to visit during this time, but it’s truly one of the most special seasons to venture to this part of the Hamptons. But be warned, you shouldn’t go expecting a scene of any sorts. Many restaurants and establishments are closed, so it’s a bit of a ghost town, but it’s the perfect time to appreciate the area’s stunning natural beauty. Plan to go on plenty of hikes, take in the scenic views and the wildlife, and enjoy a weekend of relaxation and serenity. Here, our guide on where to eat, sleep, and play in Montauk during the winter.

Where to Stay
Gurneys Montauk Resort & Seawater Spa

Though most of Montauk’s top hotels shut down for the winter season, Gurney’s keeps its doors open as the only four-season resort in area. The historic beachside hotel is just a short drive from town, or if you don’t want go anywhere, the property has a host of dining options, including LDV Hospitality’s Scarpetta Beach, The Regent Cocktail Club, and Corso Coffee. Plus, you'll find a full roster of on-property activities and events for the winter to keep you entertained, including an open-air ice skating rink (new this year) where you can sip hot toddies and get your Michelle Kwan on while taking in sweeping views of beach.

Day 1
Either drive, take the LIRR train or the Hampton Jitney from Manhattan out to Long Island’s furthermost point. Once you arrive, recover from the long ride with a spa treatment at Gurney’s. It’s a full-service spa offering treatments ranging from manicures and pedicures to deep tissue massages and detox therapy. Next, grab lunch at Tillie’s, which features a menu of seasonal, classic American favorites. Spend your afternoon exploring Montauk’s stunning natural surroundings. Layer up, as it will be chilly, and go for a stroll or run right along the beach. If you head east, you'll pass stunning waterfront estates and eventually end up in town. Or, take a drive to Montauk Point State Park and make sure to look out for seals—the winter is prime seal spotting time here. Also, go and check out the historic Montauk Point Lighthouse (the oldest working lighthouse in the state). Close out your day with a visit to Montauk Brewing Company. We’re partial to the Offland IPA, but they also have Driftwood Ale, Summer Ale, and Arrowhead Irish Red Ale (all hand-crafted). Call them before you go to get their latest winter hours. 

Day 2
Start your morning with breakfast at the famous, local favorite John’s Pancake House. In the summer, it’s hard to get a seat at this Montauk institution, but during quieter times it’s usually a breeze. They have several different pancake options (from berries to chocolate chip), so it’s a good day to splurge on carbs. Afterwards, head to Joni’s to pick up wraps and salads to bring on your hike along Ghost Town Trail in East Hampton. Before you go on the three-mile journey through the historic Northwest Settlement, make sure to download the guide and map provided by the East Hampton Trails Preservation Society. Afterwards, make the short drive to Wolffer Estate for a tasting. Close out your trip with a little ice skating, warm drinks, and dinner at Scarpetta back at the hotel.