The North Fork of Long Island has always been likened to the wrong side of the tracks. While the South Fork has prospered as an affluent resort community since the late 1800s, the North Fork has remained largely undeveloped, mostly because the beaches on Long Island Sound tend to be littered with rocks and sharp shells. Yet as the Hamptons have become a bumper-to-bumper media circus overrun with cell-phone-wielding rubberneckers, many tastemakersand power brokers have decided to head north, across the bay, in search of traffic-free lanes and logo-free sunsets. Notwithstanding a growing number of wineries (New Line Cinema President Michael Lynne recently bought two), the peninsula is still a patchwork of lush potato fields, colonial and postwar architecture, rickety farmhouses, and funky seafood restaurants marked by the ubiquitous lobster trap and captain’s wheel. “It has a blue-collar charm that doesn’t make you feel as if you’re in the middle of a photo shoot,” said Simon Doonan, the creative director of the department store Barneys New York, who has a home on Shelter Island and is part of the North Fork/alt.Hamptons community that includes architect Richard Gluckman, screenwriter Michael Austin, and Lutèce chef-owner Eberhard Müller.

it’s always a guilty pleasure driving out to the North Fork from Manhattan when you whiz off the Long Island Expressway onto Route 25. Suddenly we had all the time in the world to stop and rummage through the thrift shops we found all along the way, which sell everything from ’70s roller skates to prosthetic legs. In Southold we pulled in at the Seafood Barge, overlooking the Port of Egypt marina, for a hearty lunch of clam chowder and fish sandwiches. The afternoon was just as lazy: tasting the vintages at Lynne’s Corey Creek; checking out the big-haired ladies reclining on plastic sun chairs and sipping canned beers while we checked in to the Silver Sands Motel. After refreshing ourselves in the pool, we ventured into town. A former whaling village, Greenport saw its heyday during Prohibition, when rumrunners used the port to transport illegal booze. Now this lively harbor town on Peconic Bay is filled with kitschy trinket shops, ’50s diners, and bars. After dinner we had drinks at the Whiskey Wind Tavern, a forbidding dive covered with American flags and neon Budweiser signs. The locals proved hospitable, however, agreeing to loan me crisp bills for the jukebox as long as I agreed to play only classic rock tunes by the Doors and Led Zeppelin. The next morning, we rented bicycles at the Bike Stop in Greenport (631-477-2432; half day, $18; full day, $22) and peddled out for a day of picnicking and collecting shells. At the very tip of the North Fork is Orient Point, an overgrown area of cattails and reeds where I recommend experiencing the underrated luxury of watching the grass grow. At dusk we ferried over to Shelter Island and Sunset Beach, a ’60s seaside hotel that was renovated three years ago by André Balazs. Despite the flotilla of hipsters who mob its festive open-air restaurant and bar on weekends, great pains have been taken to keep the vibe relaxed and beachy. Inflated beach balls came with our rooms, the staff wear flip-flops, and the celebrity regulars have to wait in line with everyone else.

Lodging

The quirky 1950s- and ’60s-style motels on the North Fork and Shelter Island are as campy as a faded old postcard. My favorite is Greenport’s 1958 Silver Sands Motel, which is still painted pink and turquoise and has the original Formica surfaces and atomic-patterned tile floors. It has a quiet private beach and a heated outdoor pool (631-477-0011; doubles, $80–$150, including two Sara Lee muffins; w). Sunset Beach, on Shelter Island, is hands down the hippest spot outside New York City. All 20 rooms face the water and have cute modern sundecks (631-749 2001; doubles, $150–$380). For something more traditional, the Ram’s Head Inn is a grand old Victorian-style hotel with a tumbling lawn and secluded beach in Shelter Island Heights (631-749-0811; doubles, $95–$225). In East Marion, Treasure Island Bed & Breakfast is pure luxury, an elegant estate overlooking the sound and Gardiners Bay, with three suites (631-477-2788; doubles, $295).

Dining

The North Fork is ground zero for down-home seafood restaurants that specialize in fresh lobster, clams, and oysters. The Seafood Barge in Southold is a perfect nautical throwback, with massive barge cleats and lots of varnished knotty pine (631-765-3010; entrées, $15–$30). Orient by the Sea is as close as you’ll get to being on a fishing boat without actually boarding one (in Orient; 631-323-2424; entrées, $14–$22). Claudio’s Restaurant, established in 1870 by a Portuguese sailor named Manuel Claudio, is a Greenport seafood joint that looks out over the harbor and claims to be the “oldest same-family-owned restaurant in the country.” Waitresses with frosty-blue eye shadow serve up portions that would be considered generous by any standards (631-477-0627; entrées, $22–$45). If you can’t stand the sight of another ornament made of driftwood, try the Japanese restaurant Sushi at Aldo’s in Greenport (631-477-1699; entrées, $16–$25). And there’s no better spot to slurp a thick chocolate milk shake than at the soda counter of Greenport’s funky old Coronet diner, which was built in 1949 (631-477-9834; milk shake, $2.50; sandwiches and burgers, $3–$7). Of course, Sunset Beach, on Shelter Island, has great citified fare—the bite-size tuna and tataki appetizer and the grilled ahi tuna with shiitake mushroom couscous were mouthwatering (631-749-2001; entrées, $18–$29).