Road Trip Bliss: Long Island

The east end of Long Island, New York, looks like the gaping jaws of a crocodile. I’m at the back of the animal’s throat, driving northeast on County Road 105, when I see the mouth opening wide in front of me. Here the reptile’s smile spreads around the Great Peconic Bay.

“Head north, head north,” I tell my husband, Tim, and the suburban sprawl so synonymous with central Long Island gives way to farmland. Hand-painted roadside signs advertise fresh eggs, raw milk, lavender bouquets. I roll down the windows, slide back the sunroof, and crank up the radio. My hand surfs up and down on the wind. I breathe deeply, inhaling salty air and a bit of dust kicked up from the road. “I love it out here,” I say, as Tim laughs. “I know,” he says. “You’re geeking out like a little kid.”

I was a kid when I first came here, out where the highways narrow to two-lane roads, where the houses grew larger, then small again, all the way out to “the End,” as the locals call it. Montauk. My extended family gathered to camp each summer at Hither Hills, an oceanfront state park outside Montauk. I learned how to ride a bike, fell in love with stargazing, and, most nights, collapsed into my sleeping bag after hours of wave jumping in the Atlantic.

Then, when I was 11, my mom and dad split up. Family vacations became casualties of an ongoing war. Neither parent ever took my brother or me back. When I met Tim, I confided that Montauk was “my happy place.” After a dozen years together, he and I have finally booked a campsite at Hither Hills. But before we ferry to Montauk, we need provisions from the island’s agrarian North Fork.

Finally I spot the large green and white house of Briermere Farms at the end of the road. “That’s it, stop there,” I tell Tim, pointing. “And get the cooler ready.” We fill our basket with plump berries, corn, tomatoes, and—the crown of our haul—one of the farm’s famous pies, a strawberry/rhubarb still warm from the oven.

As we drive east, rows of grapevines stretch out, their arms entwined like lines of family members gleefully dancing the “Hava Nagila”—almost as if the land itself is celebrating the North Fork’s evolution over the past four decades from potato to wine country.

“Good wine needs cheese,” says Tim, flashing a cheesy smile, and we turn right on Love Lane into the tiny thumbprint of a town called Mattituck. Inside the sunny Village Cheese Shop, a cherub-faced cheesemonger approaches us. “Anything in particular in mind?” asks the teen, and upon hearing our plans to visit some nearby vineyards, he reaches into the fridge—piled with some 300 varieties—and fishes out a raclette from Vermont. While carving off a sliver, he explains how it’ll keep in the warm weather. The cheese is pungent and smooth; Tim nods his approval.

Another few minutes on the road brings us to Shinn Estate Vineyards. Thwack-thwack, thwack-thwack. I hop out of the car to discover a windmill spinning frantically—and loudly—overhead. We slip into the recesses of the rustic tasting room, in a 125-year-old barn. A border collie immediately plops his head in Tim’s lap.

Owner and winemaker Barbara Shinn comes over to check on her sidekick, Panda, and offers us a pour of the estate merlot while explaining that the windmill and solar panels help power the vineyard, and organic, biodynamic methods use the natural yeast that develops on the skin of the grapes. “It looks like lavender baby powder,” she says.

Shinn’s husband and co-owner, David Page, weaves us around massive silver tanks. He tells us how the couple had opened one of Manhattan’s first farm-to-table restaurants in 1993 in Greenwich Village. Now they infuse their vineyard with the same locavore sensibility. “Foraging at its finest,” I tell Tim as we pick up a few bottles on our way out.

The sun begins to dip as we head farther east along Route 25, past plots of spinach and sunflowers, clusters of low-slung motels, and marinas and marshes. A bridge lifts us over train tracks; the sun glows over the pine barrens like the wick of a snuffed-out candle. From there it’s a short way to our stop for the night, Greenport, a 17th-century English settlement turned 19th-century whaling and shipbuilding hub. Now it’s a seaside tourist magnet, with B&Bs and upmarket dining such as Peconic Bay scallops at the Frisky Oyster.

On our way to dinner, I wander into one of Greenport’s many boutiques, the White Weathered Barn. I tap Tim’s shoulder to show him a rather clever souvenir, a flattened-out fork with “North” pressed into the metal. As we walk past Greenport’s centerpiece—an antique 1920s carousel encased in a sparkling glass structure overlooking the harbor—shrieks of laughter break out. Children clamor on the edges of their horses, eager for their prize: a brass ring that guarantees another ride.

The next morning, we pull up behind a milk truck onto the small North ferry. Before reaching the South Fork, we must pass through Shelter Island, an 8,000-acre spot of land (a morsel in the croc’s mouth). I pop open the car doors to watch sailboats slide through Gardiners Bay; a few leather-clad motorcyclists unstrap their helmets and stretch their faces up like cats toward the light.

The eight-minute drive across the island winds us past the Victorian cottages of Shelter Island Heights and along the Mashomack Preserve. I’d love to explore its 20 miles of hiking trails, but I’ve got Montauk on my mind.

“The North and South Forks have different personalities,” I begin to tell Tim as we disembark the South ferry. On the weekend, the roads out here clog with traffic from the East Coast elite who make the Hamptons their summer playground. Just then, a cherry red Alfa Romeo Spider convertible pulls up as evidence.

In Sag Harbor, we stop to stretch our legs and wander past the main drag’s old hardware shops and an art deco theater. At a housewares boutique called MONC XIII, I spy a Coleman cooler identical to the one in our trunk, only this one is encased in supple leather. It costs $835. As we race back to our car, suppressing laughs, Tim wonders how one manages to put anything in a leather-clad icebox without destroying its finish. “It’s a cooler—it gets dirty!” he mutters.

Continuing south on Route 114, I point out how the hedgerows grow taller and the homes get farther apart. “This is East Hampton,” I explain, rolling my eyes, and we take a quick detour down Dunemere Lane to ogle the thatched-roof Maidstone Club, a storied country club for the billionaire set.

It’s been more than 20 years since I visited Montauk, and as we drive through the town of Amagansett, my stomach twists into knots. I’m nervous the creep of the Hamptons has overtaken my Montauk. Over the past few years, I’ve seen its beaches become backdrops in hip magazine spreads.

Still, the drive remains the same. The scrub pines get shorter, and the road narrows at the Napeague isthmus, or “water land” as the Algonquins called it, past a series of lobster and clam shacks. As we skim over hills toward town, my stomach jumps, my nerves giving way to excitement. As if on cue, the chorus of Ellie Goulding’s “Lights” comes on the radio: “Calling, calling, calling me home.”

We pull into Montauk’s circular town plaza, where I’m happy to see the old Memory Motel, immortalized by the Rolling Stones, holding on, albeit near a Cynthia Rowley designer boutique and an outpost of Manhattan’s fashionable Momofuku Milk Bar. “Save Montauk” signs—with a red slash through a trendy fedora—have been posted around town. I worry I’m already too late. I’d hate to be perceived as another hanger-on.

Suntanned 20-somethings swarm the elevated deck at the Sloppy Tuna beach bar, but I’m relieved to see tradition enduring at the Shagwong Restaurant, with dapper waiters in ties and tan blazers. At hotels like the Surf Lodge, Sole East, and Ruschmeyer’s, a see-and-be-seen crowd angles for space among boho-chic tepees and picnic tables.

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“It’s hard to get a fisherman’s rate these days,” admits Ken Walles, owner of the Oceanside Beach Resort, when we run into him in town. He has painted over his hotel’s famous highlighter yellow facade, save for a set of three smiley faces on its east-facing wall. “The town is changing, but you change with it,” he says.

Back in the car, we continue east to the brown-and-white-striped Montauk Point Lighthouse. “We’ve made it,” I say. “The End.” Tim and I skip stones and dip our toes in the Atlantic. My arms wrapped around his waist, we linger to let the new memory set in.

Our campsite at Hither Hills is calling, but first I instinctively throw a left off Montauk Highway. Every summer my grandparents, now gone, checked into the East Deck Motel, its blue neon sign overlooking the cliff-sided Ditch Plains beach. The sand is nearly purple, having been dredged up in a recent storm. A handful of surfers bob on their boards, waiting for the perfect wave.

The sky has begun to blush as we make our way to set up camp. Then I see it—the brown wooden sign with carved white lettering: Hither Hills. The flagpole clangs in greeting. Children scurry from the bathhouse wrapped in towels, their lips waterlogged and blue. Seagulls look up expectantly while we unpack our tents and cooler—no leather, but it’ll suffice—stuffed with North Fork goodies.

Kids are pedaling circles on their bikes, and the smell of charcoal mingles with the sea air. It’s just as I remembered—only better, because I’m back.

Janelle Nanos, a former editor at Traveler, grew up in central Long Island and is currently an editor at Boston Magazine. Follow her on Twitter @JanelleNanos. This piece originally appeared in the June/July 2013 issue of National Geographic Traveler magazine.

> Other Highway Highlights:

  • Cutchogue Village Green: 
Christened the “principal place” by the Algonquin Indians who once inhabited Long Island, Cutchogue is one of the U.S.’s prime sites for seeing original English architecture (with free tours on weekends).
  • North Fork Table & Inn: Renowned for its upscale menu (truffle 
risotto, pan-roasted local scallops), this Southold destination attracts Manhattan foodies and recently introduced a lunch truck parked in the lot outside, serving pulled pork sandwiches and lobster rolls.
  • Greenport Harbor Brewing 
Company: Locavores who tire of North Fork wine find another 
island sip in this tasting room next to Greenport’s tiny town jail. Try the Harbor Pale or, if it’s on hand, the rare Triton barley wine, named for the Greek messenger of the sea.
  • Mashomack Preserve: This tranquil Shelter Island park—sometimes referred to as the “Jewel of the Peconic”—features more than 20 miles of hiking trails, 12 miles of coastline, and one of the East Coast’s largest osprey populations.
  • Lobster Roll: This seaside shack in Amagansett, on the Napeague isthmus, claims to have invented the “cold” lobster roll. Locals just call it “Lunch,” thanks to the prominent neon sign on its roof.
  • Montauk Point Lighthouse: New York’s oldest functioning lighthouse was commissioned under George Washington in 1792.
  • Parrish Art Museum: Founded in 1898, this art gem moved to Water Mill last fall. Architects Herzog & de Meuron designed two low-profile wings that run in parallel, mimicking the forked geography of the island. Sky-lit galleries showcase works from the storied artists colony of eastern Long Island, most notably 40-plus pieces by William Merritt Chase.

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