Where to Stay, Eat, and Shop in Montauk This Fall

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," is in the fall, when the weather still sparkles and the crowds have cleared out. Here's everything you need to know for an escape from the city.

Getting There

Montauk is approximately 120 miles from New York City — upwards of three hours by car or the Hampton Jitney bus. The trip takes a little more than three hours by Long Island Rail Road. The most direct driving route is the Long Island Expressway, to exit 70 (Manorville), then Route 27 East all the way to the end. For a more scenic route, detour onto the Old Montauk Highway in Napeague.

Stay

Gurney's Star Island Resort and Marina sits on lake Montauk, right in the middle of all the action. Showfish, the buzzy on-site restaurant, has incredible and inventive dishes like lobster with fermented sriracha and ginger. The property offers marina access, lounge chairs on a private beach with kayak and SUP rentals included, and three pools. Another option is Marram — a luxury beach-front oasis with direct Atlantic-beach access, fires for s'mores, and art by Sean Spellman. The resort has a variety of activities throughout the day available to guests. Wake up and enjoy meditation and yoga overlooking the beach, indulge your creative side with art workshops for the entire family, or participate in a guided nature walk.

Eat

After riding the morning waves, everyone gathers for breakfast burritos and chai lattes at Joni's. Hello Coco at the Breakers Montauk is a great lunch spot, serving island-style dishes like salmon poke and fish tacos. Looking west over Fort Pond Bay and Gardiner's Island is the best sunset spot in town, Navy Beach. And the expansive menu compliments the natural show with mouth-watering items to please any pallet. La Fin, which opened its doors in 2021, features hyper-local, sustainable ingredients prepared thoughtfully in the French tradition. Order the lobster cavatelli with anchovy bread crumbs and the local fluke ceviche.

Shop

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, mid-century modern vases).

Surf

Don't miss Ditch Plains, with its legendary offshore break and wide beach bracketed by jagged cliffs. If you want to take surfing lessons, Marram offers classes or head to the Sunset Surf Shack and ask for Craig Lieder Jr., a quintessential hang-ten dude.