The Un-Hamptons

Leave your pretensions behind at Montauk, the beach town that prides itself on being different from its tony neighbors.

Long Island

Cover Story


I swear I see Jay Gatsby checking in. Broad-shouldered, blond and wearing a tan linen suit, the man swaggers into the hotel with Redford confidence and leans into the dark, wood counter where an attendant asks his name. Is he holding a fedora? I blink twice. I'm just imagining things. I've felt like a part of F. Scott Fitzgerald's novel The Great Gatsby since I arrived at the Montauk Manor. It's as though my flight from BWI to Long Island and my two-hour drive to Montauk, the easternmost town of the island's sea-flanked south fork, transported me back through time.

I'm reading in the hotel's lobby, a grand throwback to the opulence of the 1920s, when money flowed like water. Gleaming slate floors stretch in front of me for what feels like the length of a football field. A dozen wide arches meet with columns that run parallel on both sides of several medieval-looking chandeliers. Under each arch is a set of plush couches, some in front of crackling fireplaces, others in front of 15-foot-high windows. At the corner of the lobby is a baby grand piano set on auto-play.

The comparison to Gatsby's time isn't a stretch. Carl Fisher, the wealthy developer credited with building Miami Beach, envisioned the rural, oceanside town of Montauk as the "greatest resort in the world." He planned to dock cruise ships in the port and cover the rolling hills with Tudor-style mansions.

Montauk Manor, a 170-room, four-level English Tudor hotel built atop Signal Hill, the highest point in Montauk, was the crown jewel of his vision. When it opened in 1927, there were 200 waitstaff who served high-society guests such as the Vanderbilts.

When the stock market crashed in 1929, Fisher's dream for the area was forgotten. He couldn't afford the upkeep of the hotel and few could afford to stay there. By the mid-1930s, the manor -- and an era -- was largely an afterthought, allowing Montauk to become the down-to-earth beach town it is today.

"Lucky for us," says Diane Koelpin, who runs the hotel today. "It would have been a very different place if Fisher had his way."

Montauk Manor sat idle on and off for years until 1987, when the grandiose skeleton was restored, undergoing a $20 million renovation.

Step outside the hotel and you'll find little in the rest of the town that resembles its high style. The area prides itself on being the least pretentious place on the east end of Long Island. Diamonds don't dangle from the wrists of beach-goers like they do in the nearby Hamptons. High-rise resorts do not line the oceanfront. Forget boardwalks -- locals may take offense if you ask where one is.

The beaches are rugged and windswept. Hotels and motels are rarely higher than two stories, and few are directly on the beach. Seals sun themselves along oceanfront rocks several months of the year.

Residents wear T-shirts that read "The End," celebrating the town's position as the last stop in New York before England. The only bragging you'll encounter is down near the docks, where fishermen sometimes hang their impressive deep-sea catches.

You can plan every day of your trip from atop the grounds of Montauk Manor, which provides a near-360-degree view of the area.

Look east and you'll glimpse the lighthouse and an old radar tower in Camp Hero, an Air Force base turned state park. Just before it, your eye will meet up with Lake Montauk, where fishing boats depart into Block Island Sound every morning.

To the north is Fort Pond Bay, a great place to kayak. You might glimpse a hillside nestled amid Deep Hollow Ranch, a cattle ranch established in 1658. Stretching out in the distance from the hotel's main doors -- it's a 10-minute bike ride to the beach -- are miles of uncrowded strips of sand lining the Atlantic Ocean.

If you picture eastern Long Island as Manhattan's suburban sister, dotted with subdivisions and traffic jams, you're in for a surprise.

"When people come to Long Island," says Tom Dess, superintendent of Montauk State Parks, "they don't expect to see this."

Watering holes

Anyone who knows beach towns understands that summer isn't a season -- it's a culture. Montauk's residents live most of the year with half their town boarded up. Even the tiny movie theater shuts down when the summer ends.

Locals look forward to May, when they can finally break out their kayaks, sailboats and fishing poles. Throngs of tourists descend on the town each season, and locals welcome their arrival. Many residents' livelihoods depend on tourism.

But even with all the tourists, the area never feels crowded, and the beaches remain fairly quiet.

Ask anyone about the coolest beach spot, and they'll direct you to Ditch Plains. It's thought of as one of the best surfing spots in the Northeast, with waves as high as 12 feet. Rain or shine, you can see dozens of surfers bobbing like leatherback turtles about 200 feet out from the shoreline. Boys balanced with the grace of ballerinas ride the waves in.

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