First came the fishermen. Then came the surfers. Now the formerly scruffy enclave of Montauk, at the easternmost point of Long Island, has been colonized by fashion-forward boutiques and hotels that are one-upping the rest of the Hamptons with a refreshingly relaxed sense of style. The best time to head to “the End,” as locals call it, is in the fall, when the weather still sparkles and the crowds have cleared out. Here, everything you need to know for an escape from the city.
Montauk is approximately 120 miles from New York City—upwards of three hours by car or the Hampton Jitney (hamptonjitney.com; one way from $30) bus. The trip takes three hours by Long Island Rail Road (mta.info; one way from $15). The most direct driving route is the Long Island Expressway, to exit 70 (Manorville), then Route 27 East all the way to the end.
T&L Tip For a more scenic route, detour onto the Old Montauk Highway in Napeague.
Owned by a team of New York City club impresarios, the Surf Lodge (doubles from $275) made a splash when it opened its 32 waterfront rooms this summer on Fort Pond. There’s a tiny Tracy Feith shop filled with retro caftans, a restaurant helmed by Top Chef star Sam Talbot, surf movies on rotation 24/7 in the lobby, and an open-air deck that doubles as the Hamptons’ hottest nightspot. Much more low-key are sister properties Solé East (doubles from $220), in a Tudor-style building with sisal carpets and wood-burning fireplaces, and Solé East Beach (doubles from $160), in a revamped oceanfront motel. Also on the radar: the 80-year-old Montauk Yacht Club (doubles from $289), where Charles Lindbergh once visited; its 107 rooms will undergo a multimillion-dollar overhaul during the next year.
Manhattan, Tokyo—and Montauk?Vintage boutique Screaming Mimi’s chose this unlikely location for its third outpost. Former models Marylynn Piotrowski and Staci Dover are the tastemakers behind Tauk, the source for bright espadrilles, sailcloth totes, and other beachy finds. Striped Breton sailor tops hang from driftwood displays at
Share with Montauk, which highlights fair-trade and organic products; its owner, Joelle Klein, used to be a designer for Calypso Christiane Celle. Surfer chicks—and their moms—love Haven for its flirty frocks, Brazilian jewelry, and vintage finds (a Pucci longboard, Midcentury Modern vases).
After riding the morning waves, everyone gathers for breakfast burritos and chai lattes at Joni’s (breakfast for two $20). The Gig Shack (lunch for two $56) serves “global surf cuisine,” including fish tacos and a soft-shell crab BLT; local musicians drop in to perform acoustic sets. Tucked in the back of a marina, the open-air Hideaway (dinner for two $54) is worth seeking out for its grilled Mexican corn on the cob. A block from the ocean, Runaways Bar & Grill (dinner for two $86) is the spot for just-caught seafood, such as flounder stuffed with lump crab.
Don’t miss Ditch Plains, with its legendary offshore break and wide beach bracketed by jagged cliffs. If you want to take surfing lessons, head to the Sunset Surf Shack ($60 per hour) and ask for owner Craig Lieder, a quintessential hang-ten dude.