Now that Montauk has become so over-crowded in the summer (nearly every bar and restaurant hinges on “if you can get in”), winter is an even better time to visit. Enjoy having the place (mostly) to yourself, and take advantage of discounted resorts and hotels (do a spa day at Gurney’s). The monochromatic drama of The End in the off-season is perfect for a relaxing weekend getaway (especially a romantic one)—it’s very all Eternal Sunshine of the Spotless Mind. Though, of course, if it is a couple’s trip, we hope things end up better for you than they did for the characters in that movie. Nevertheless, our recommendations include locales in Amagansett and Montauk only, since they have a more similar vibe than the other Hamptons you pass on the train while riding the Friday afternoon cannonball. We’ve included our favorite spots for those days and nights spent out east, well, as far east as you can possibly get on Long Island.
PUT ‘EM BACK
Surf Lodge // 183 Edgemere St, Montauk, NY 11954
Of course, this would be our first pick—but if we didn’t recommend Surf Lodge, we would just be lying to you, and to ourselves. Make a brunch reservation on Sunday so you can stay for the rest of the day (the line to get in snakes up Edgemere on most evenings). Hint: for those looking for a respite from the relentlessly trendy crowd, if you head left when walking towards the water, there is a more private lounge area. So, relax, order endless Endless Summers (a delectable vodka concoction), and watch the sun set over the lake. At night, the scene becomes clubbier, but the concert series is epic, and the Flaming Lips performance was simply life-changing. So, if you see one of your favorite acts on the line-up: book now.
The Point // 697 Montauk Hwy, Montauk, NY 11954
If you want to relive your favorite college bar, head downtown to The Point. Tom Petty will be playing, shots will be ordered, and chaos will ensue. Hint: if you get downtown early, head over to the front door to get your wristbands for both The Point and the Memory Motel (which you’ll likely be heading to afterwards). Hint: dancing in front of the fan in the main bar area minimizes sweating (which will be inevitable), and provides a great wind machine for your dance moves.
Memory Motel // 692 Montauk Hwy, Montauk, NY 11954
The Memory Motel may be the most inaccurately named watering hole of all time considering it is often the site of no-recollection. The dance floor will be flooded, and you will be stomping around in the slush with a Bud Light in one hand, and a fist pumping in the other. Don’t say we didn’t warn you.
Stephen’s Talkhouse // 161 Main St, Amagansett, NY 11930
A bit of a trek coming from Montauk, but nevertheless worth the cab fare, Stephen’s Talkhouse is an Amagansett institution. Go for the 90s cover bands, and to explore the endless indoor/outdoor areas for drinking, dancing, and socializing. Expect endless run-ins with friends, and friends of friends. Head there early to avoid the line.
IF YOU CAN GET IN
Montauk Yacht Club // 32 Star Island Rd, Montauk, NY 11954
The only private cub in Montauk with a marina, so see if a friend can take you out on their boat to see how the other half lives. The ostentation of the mega-yachts lining the docks is offset by the nautical chic décor inside the clubhouse. A stripe-lover’s dream.
Montauket // 88 Firestone Rd, Montauk, NY 11954
This bar hosts some of the best sunsets in Montauk. Come here for sundown to mingle with the locals and to post up around the large, wooden bar for a drink or three.
Lynn’s Hula Hut // 426 W Lake Dr, Montauk, NY 11954
This Tiki bar is perfect if you want to get weird with your friends in a less-crowded environment downtown. The ambiance is that of a Hawaiian luau transferred to Long Island.
The Hideaway // 364 W Lake Dr, Montauk, NY 11954
Who wouldn’t want to eat Mexican food in a hot parking lot? (RIP to the golden age of Cyril’s—though it was warm milk we were consuming, not enchiladas). Sometimes, Mexican food is the only thing that will do, and this place offers up the best of the best.
The Dock // 482 W Lake Dr, Montauk, NY 11954
This restaurant is supremely local, with a dark wooden interior decorated with funny (punny) and perverted old signs warning of loose women and drunken sailors. No cell phones allowed, and cash only, so play by the rules, because they’re not in the business of courting tourists.
Swallow East // 474 W Lake Dr, Montauk, NY 11954
This spot on West Lake Drive now has its own late-night scene too, but dinner is still not-to-be-missed. The wooden interior of the restaurant has long tables that are perfect for groups, and most of the tables overlook the water. Also, the food is superb.
Ruschmeyer’s // 161 2nd House Rd, Montauk, NY 11954
Get a table outside, and enjoy the swings and corn-hole before heading inside for the evening to hit up the dance-floor. Order their signature cocktail—it’s tasty yet deadly. Trust us on this.
Duryea’s // 65 Tuthill Rd, Montauk, NY 11954
Amazing lobster shack right on the water. Order a lobster roll and sit out on the dock for the sunset—it’s super romantic, and also, super cheap.
Crow’s Nest // 4 Old West Lake Dr, Montauk, NY 11954
A cult favorite, people are clinically obsessed with having dinner at this place. Check it out to tell your friends you went there, or else you’ll never hear the end of it.
GET YOUR FIX
Goldberg’s // 28 S Etna Ave, Montauk, NY 11954
An institution—get the bagels, obviously.
Ditch Witch // 40 Deforest Rd; Montauk, New York 11954
Cleverly named shop offering delicious sandwiches (in case you couldn’t have guessed).