Montauk just isn’t like other beach destinations on Long Island. Sure, it has white-tablecloth dining, posh boutiques, and lovely places to sip a martini. But unlike the Hamptons, this town has the naturally salty flavor of a windswept coastal town that about 3,400 proud residents care for all year round.
Come summer, those locals adapt to and even welcome the dramatic influx of New Yorkers and other regional tourists, some of whom have escaped here for generations. They come for the easygoing flavor of this historic oceanside town, where recreation, fresh seafood, and a legacy of leisure are what it’s all about.
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Kick off the weekend with the always-fun vacation game known as “what should we eat?” Luckily Montauk has loads of great choices. Navy Beach, located on the sandy shore of Fort Pond Bay, will get you in the right frame of mind with a full menu of mussels, scallops, and other seafood dishes. For something more casual, duck into the Montauk Bake Shoppe on the central plaza for wraps, sandwiches, and panini.
The circular plaza is the town’s hub, and from there you can browse familiar upscale shops like Cynthia Rowley or Calypso, or head to the old-school White’s Drug and Department Store to stock up on flip-flops, Frisbees, and other essential beach gear.
Just off the rotunda, grab an ice cream at John’s Drive-In, and then burn off those calories with a rental from Montauk Bike Shop (daily or hourly rates available; no reservations needed). The friendly staff there will help map out your perfect ride, like a scenic 12-mile round-trip jaunt to the Montauk Lighthouse—which, by the way, is a national historic landmark whose museum explains its tie to George Washington. Cruise the rolling hills of Montauk Point or Camp Hero state parks, or park your bike for a scenic hike along the shore.
When dinnertime rolls around, you can’t go wrong with Salivar’s Chowder House at Westlake Marina. Home to arguably the best seafood chowder in town, the restaurant also has a sushi bar, indoor and outdoor seating, and a top-floor deck overlooking the harbor. Alternately, next door is the more atmospheric Swallow East, serving inventive small plates made for sharing and zingy cocktails suited to the dockside locale—with outdoor movies every Friday night (and live reggae on Sundays).
Fuel up for a fun day at Joni’s Kitchen, a standout breakfast and lunch eatery serving delicious, healthy-leaning meals like egg-white breakfast wraps, açai and quinoa bowls, and a kids’ menu that’s light on the deep-fried foods for a change.
Recreational options abound on a typical summer day in Montauk. For anglers, reserve ahead at Montauk Fishing Charters for a full- or half-day excursion to catch striped bass, cod, tuna, flounder, and other fish. Horseback riding is a family-friendly option, made even cooler by saddling up at Deep Hollow Ranch—the oldest working ranch in the country, established in 1658. If the waves are calling, head to Air and Speed Surf Shop to rent gear, take an offshore lesson, or sign up the kids for surf camp.
Opt for a more laid-back Saturday at the lakeside Montauk Yacht Club, where you can catch live music every weekend afternoon on the great lawn. You can sip drinks, stroll the marina, play volleyball or bocce, and grab a lobster roll at the food truck parked on site in July and August.
It’s amazing how vacationing can work up thirst. Quench it at local haunt The Dock, where you can enjoy an authentic no-nonsense, crusty-sailor kind of vibe—and adhere to “the list” that includes no screaming kids, no whining, no cell phones, and no sensitive drunks. There you can sample daily-caught seafood, soft-shell crabs, clams on the half shell, and homemade desserts. If you’re over seafood, there are juicy burgers and pasta on the menu too.
A more polished alternative awaits at Gosman’s Dock, a family-run property open since 1943, and home to both casual and upscale restaurants, as well as a retail fish market. Or you can head downtown for a beer and a bite at Shagwong—which, despite the sound of its name, is not a Chinese restaurant. Under new ownership since 2015, this vintage Montauk tavern is still a comfort-food mainstay known primarily for its lively bar.
Round out your weekend’s activities with a Sunday morning tee time or driving-range bucket at Montauk Downs State Park Golf Course. Traveling with kids? Maybe mini-golf or a paddleboat rental at Main Street’s old standby Puff ‘n’ Putt is a better fit.
One of the best casual restaurants that isn’t high on the radar of most tourists is the Hideaway. It’s located in the Diamond Cove Marina and is so nondescript from the outside you may wonder if you’re in the right place. Wander around to the side entrances to feast on excellent Mexican or BBQ plates at sweet prices, topped off with a Mexican soda, tequila, or fruity sangria.
Also off the main drag but worth the drive is Melet Mercantile. Though it has a showroom in Manhattan, Melet’s Montauk outpost has an impressive selection of fine vintage beachwear for all ages, plus accessories and art. Although they may be out of most people’s budgets, the inventory here is cool enough to warrant some quality browsing anyway.
For those heading home on Sunday, consider a last-stop souvenir from the centrally located Montauk Brewing Company. Grab a six-pack of Driftwood Ale or maybe a seasonal brew to conjure your weekend memories later on.
On the other hand, if you’re lucky enough to extend your weekend, cruise over to the Montauket on the edge of Fort Pond Bay. It’s part real-deal-retro inn (as in, they have no website but are already booked all summer); part fish shack; and, most important, a great western-facing spot where you can relax and enjoy the ultimate vacation spectator sport: watching the sunset.
WHERE TO STAY
For such a small town, Montauk has no shortage of motels, hotels, AirBNBs, and other short-term rentals. The key, as always, is to reserve in advance, and be prepared for the sticker shock of high-season rates.
The Montauk Yacht Club has lovely, high-end accommodations with the added bonuses of a marina (with slips for rent); an on-premises spa; plenty of amenities and activities; a friendly bar with excellent wine and cocktails; and two restaurants. The Surf Lodge (from $295) is a hip hotel that lets its rustic-chic style shine, with a sophisticated restaurant and an almost-daily on-site wellness program. The breezy Ocean Resort Inn (from $329) has a courtyard and pool area for lounging, friendly staff, and, perhaps its best feature, a nice location near Montauk’s central plaza.
It’s a hearty three-hour drive to Montauk from Manhattan along the Long Island Expressway, although it’s far easier to endure summer traffic jams aboard the tried-and-true Hampton Jitney or its luxury-bus alternative, the Ambassador. Skip the highways altogether via the Long Island Rail Road to Montauk (the LIRR’s eastern terminus).