Infinitely farther from the Hamptons in temperament than in driving time, low-key Montauk has the easygoing aura of end-of-the-road resorts from Key West, Fla., to Homer, Alaska. One of the few indications it's even aware of its just-folks allure is the droll sign that's graced the window of Shagwong Restaurant about as long as anyone remembers: "Piano player wanted. Must have knowledge of opening clams.”
Montauk would be a very different place if the 1929 stock market crash hadn't cut short developer Carl Fisher's plan to make it Miami Beach North (remnants include the Tudor-style Montauk Manor condo resort and a red-brick office tower jutting above the low-rise business district like a sawed-off sequoia).
Overall, the community remains a happy melange of fishermen's shanties, family-friendly (and often family-run) lodgings plus a few tony addresses such as Montauk Yacht Club and Gurney's Inn Resort & Spa.
Party central is a few motel-crammed blocks between the Atlantic Ocean and Main Street. Several miles north, along the western side of vast Lake Montauk where it opens into Long Island Sound (via a breach punched by the Army Corps of Engineers to create a safe haven for the fishing fleet after the 1938 hurricane decimated the old port), is the settlement of Montauk Harbor. It's a laid-back jumble of charter/party fishing/excursion boats, plus every type of eatery from clam shacks to those that actually ban bare feet and define sauce as something more than plastic packets of ketchup. The tourist center there is Gosman's Dock, started years ago as a boater's pit stop and now a seasonal waterfront mall of sorts.
Montauk is revered for its sportfishing and its ocean beaches -- which stretch east to Montauk Point and west along roller-coastering Old Montauk Highway to Hither Hills State Park. But it offers a dollop of history, too. Second and Third House Museums are actually both second versions of 18th century settlers' homes (First House wasn't rebuilt even once after it burned down).
Indian Field burial ground, off East Lake Drive, is the last piece of Long Island owned by the Montauk Indians. Off-season? Deep Hollow Ranch, which bills itself America's oldest cattle ranch (the nation's first cowboys were riding and roping on the site in the mid-1600s), offers beach/trail rides year-round. Hikers who need a focus other than the crashing surf can join winter seal walks. The seals, of course -- like other true escapists -- are always there.
