1. Where to Stay
Take a pass on Montauk’s dated, overpriced beachfront motels in favor of a recently renovated room at the Sunrise Guest House (from $125; from $150 after June 21), less than a mile west of town and a mere 300 feet from the beach. To save a few bucks, book a room without views—you can still gaze at the ocean while sipping your morning coffee on the back porch.
The brand-new Lakeside Inn’s (from $190) modern, minimally decorated rooms have fabulous decks and oversize showers with river-rock floors and teak ceilings. The inn piles on the freebies: There’s a complimentary glass of Champagne every evening, beach-cruiser bikes for morning exercise, and paddleboats and kayaks for lazy floats on the adjacent Fort Pond.
Formerly the Shepherds Neck Inn, the resortlike Solé East reopened on June 7 (from $160; from $240 after June 29) with updated rooms sporting hardwood and black-slate floors. The inn provides free shuttle service to and from the Jitney and train station, and will even taxi guests to the beach—great if you don’t feel like lugging your gear fifteen minutes to the dunes.
2. Where to Eat
Watch surfers get first breaks at Ditch Plains while you eat breakfast at Ditch Witch (40 Deforest Road; no phone), a takeout wagon in the East Deck Motel parking lot. This popular, family-run stand whips up fantastic iced coffee and breakfast burritos, plus a killer sesame-noodle salad.
Lunch alfresco at the BYOB seafood shack Duryea’s Lobster Deck overlooking Fort Pond Bay. Order a lobster roll or the broiled flounder with coleslaw and baked potato—a pager will signal when your food’s ready. For booze provisions, detour to Finest Kind Wines & Liquors (552 WestLake Drive; 631-668-9463) near the harbor and take advantage of great recommendations, like a Macon-Lugny Les Charmes Chardonnay, for under $10.
668 the Gigshack (782 Main Street; 631-668-2727) turns out fantastic Latin-inspired dishes, barbecue plates, and fresh seafood. Pair the Moroccan lamb sliders or the Montacos, fresh-fish tacos with mango salsa, with one of 30 beer choices.
A reservation at secluded Harvest on Fort Pond is worth the necessary advance planning (reservations must be made exactly one week ahead). Tuscan-inspired dishes like bruschetta with mixed seafood and penne with sautéed asparagus, mushrooms, and mascarpone cheese are served family style—three dishes plus a couple of appetizers can easily satisfy a party of six, with leftovers to spare.
3. What to Do
Though Southampton and East Hampton get all the attention, Montauk’s natural beauty is unrivaled on the East End. Over 500 feet of beautiful, clean, and uncrowded sand can be found at Kirk Park Beach, just west of the village, beside the IGA market. Public parking—a rarity in these parts—costs $15 per day.
A half-mile east of Montauk, Shadmoor State Park features unique, moorlike terrain and elevated platforms offering spectacular vistas. Hike the 1¼-mile loop trail through the scrubland, gawking at panoramic ocean views from the tops of 70- to 100-foot bluffs.
For some of the best mountain biking on Long Island, rent wheels from Montauk Bike Shop (from $9 an hour or $35 a day) and make the classic, hilly pilgrimage to the Montauk Lighthouse. Or pick up a $7 Ride Guide and explore the many trails and vistas in sprawling Hither Woods, west of the village.
The jetty at Ditch Plains Beach creates consistently rideable waves, suitable for both long- and short-boarders and beginners. When it gets too crowded, seasoned surfers should check out the breaks at Turtle Cove (located below the Montauk lighthouse) or Camp Hero State Park. Rent boards or sign up for lessons at Air and Speed Board Shop (795 Montauk Highway; 631-668-0356).
After toweling off, join the regulars at the traditional countdown-to-sunset cocktail hour at the Montauket (88 Firestone Road; 631-668-5992). Grab a picnic table and a piña colada and cheer along with the crowd as the sun dissolves into glimmering Fort Pond Bay.
4. Insider’s Tip
Taking a yoga class in the Hamptons can be a pricey proposition. Not so in Montauk, where you can find classes in airy settings for as little as—nothing. Inside a pretty pavilion in Kirk Park, Jivamukti expert Jane Beltz (631-804-1748) leads by-donation classes (Monday and Friday to Sunday, 8:30 a.m. and 10 a.m.) often accompanied by live tambora, sitar, and flute players. Another open-air yoga class ($10) is held daily at the East Deck Motel (40 Deforest Road; 631-668-2334), located just 50 feet from the Atlantic. The sensory experience is amazing: crashing waves, sea breezes, and the intoxicating scent of wild Rosa rugosa flowers wafting over the dunes.
5. An Oddball Day
Ranching may seem a tad Wild West for the East End, but Montauk was once the terminus for huge cattle drives from the rest of Long Island. The still-roping Deep Hollow Ranch, three miles east of the village, is the oldest working cattle ranch in the country, and the only place on the East End that offers both Western- and English-style riding lessons. A half-hour trail ride ($35) alongside grazing Texas longhorns is a perfect activity for kids (age six and below). And the 90-minute, four-mile beach ride ($75) is a decidedly un-glitzy alternative to watching polo in Bridgehampton.
After working up a cowboy-size appetite, head back to Montauk Harbor to feast on a bowl of mussels in coconut milk or monkfish with three chutneys and roasted summer vegetables at the year-old Inlet Seafood Restaurant, a sustainable-minded spot owned by a group of local boat captains.
6. Related Links
The Curbed offshoot, the Beach, posts obsessive WeatherDesk reports and snarky coverage of the Hamptons scene.
Check out the Montauk Pioneer, the local broadsheet published by Long Island’s much-loved Dan’s Papers.
The general tourism site On Montauk offers useful lodging, dining, and activity suggestions.