Twelve long miles of windswept road—the Napeague Stretch—flanked by pristine, often desolate parkland and dotted with several clam bar-restaurants and hotels, separate Montauk from the Hamptons, making this small seaside village feel a world apart. With water on three sides, Montauk is known for its distinct natural beauty, spectacular undeveloped beaches, parks that attract surfers and hikers, and and superb fishing.

Continue east past the friendly village center and you arrive at land's end. Here, the Montauk Lighthouse, commissioned by President George Washington in 1792 and the oldest operating lighthouse in the state, perches on a rocky bluff overlooking the wild surf and craggy coastline of Montauk Point State Park. The most spectacular sunrise on Long Island is here.

More than 50 hotels, inns, and guesthouses, along with fancy and casual restaurants and shops, are concentrated in two distinct sections of Montauk—the village center, including Old Montauk Highway, and the harbor area, which is home to the local fishing fleet as well as dozens of party, charter, and whale-watching boats.

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