Until the Road Runs Out | Long Island, NY


In mid-February, a Russian intelligence ship was spotted skulking 30 miles off the Connecticut coast, near the state’s eastern border, out past Long Island Sound where the open ocean and international waters traditionally ensure a tense politeness between nations. The story created a brief flurry of nervous amusement in my little coastal city, because although the presence of a Russian vessel wasn’t new, the specter of an American president possibly in collusion with Russia was. The ship wasn’t trying very hard to conceal itself; in fact, we knew its name, the Viktor Leonov, and its previous spying itineraries along America’s east coast, and the fact that it could carry what my local newspaper described as “a small complement of short-range surface-to-air missiles for defensive purposes only.” On the evening of the day the ship appeared, I walked along familiar downtown streets bathed in the pink light of sunset and thought how strange it was that everything was normal, yet they were out there, somewhere, and maybe they were here, too.

A few weeks later, I drive my car onto a ferry headed across Long Island Sound to Orient Point, N.Y. The route, dotted with small islands and eccentric lighthouses, seems designed to convince us there is nothing threatening nearby. I am irrationally, childishly happy, the kind of happy reserved for travel-haunted people who are on their way to places they have never been.

In Orient, originally called Oysterponds and later renamed to reflect its situation at the easternmost tip of the North Fork, I find an almost unspeakably pristine hamlet nearly abandoned for winter. Nothing this perfect is constructed on an unblemished foundation, though; I also find a little graveyard where twenty slaves lie buried along with their masters. The graves are surrounded by a neat stone wall with a white wooden gate, and a venerable tree leans protectively over one corner of the square plot. The enslaved people’s headstones are little stone nubs, while those of their owners – a husband and wife – are tall and flat, engraved with names and dates. Maybe some or all of the twenty approved of this arrangement; the story is that the masters, unable to find a local cemetery willing to bury blacks and whites together, chose to build their own instead. But I am unnerved by the feeling that the slaves may have been unwillingly held within this family arrangement even after death.

I drive west through Southold, stopping at a little parking area high above the shore. I stand at the top of the narrow wooden staircase for which the beach below, 67 Steps Beach, is named. From here, in Greenport West, I could look out past the narrow strip of sand, across the water that darkens from a pale turquoise to an opaque navy blue, and see Connecticut, after a lifetime of facing the other way.

Then I head to the contented-seeming waterfront village of Greenport. Here, along with the standard-issue graceful homes and eclectic businesses, is a surprising grab-bag of attractions, including a camera obscura and a 1920’s carousel tantalizingly wrapped in a modern-looking cylinder of glass. I am instantly enamored with the area’s many diminutive houses, which remind me of the simplest Federal, Greek Revival, or Cape Cod style homes of New England, but smaller. Searching online later, I find the terms “Greenport Vernacular” and “half houses” – with windows to one side of the front door – and “half capes.” They are tiny houses, before tiny houses got their own reality shows.

As I continue west through hamlets with names like Peconic, Cutchogue, and Mattituck, I make the first-time traveler’s instant, imperfect comparisons between my own coastline and this, its mirror image. This sliver of New York State belonged to Connecticut until 1676, and if you didn’t already know this, you could guess. There are differences, however: here, beaches drop dramatically from cliffs and dunes; there, they stretch flat beyond salt marshes. Here, vineyards are utilitarian and bunched together; there, they are less numerous and more spread out but more beautiful. Here, there is more empty space; there, parks and beaches excepted, almost every available bit of land has been built on. Preserved old schoolhouses, town greens, and farm stands and clam shacks shuttered for the off-season proliferate in both places.

When I reach Riverhead – the only town I’ve seen on this trip that doesn’t appear in permanent vacation mode and the place most like New York State and least like Connecticut so far – I make a sort of giant hairpin turn and point myself east again, towards Montauk, at the tine of the South Fork. There is a lighthouse there that I have seen in pictures and want to see in person.

But first I stop in Water Mill, where one of Long Island’s eleven extant windmills stands alone in the center of the town green. On the East End, you see wind mills everywhere, once you start to look. These simple weathered wood structures were called “smock mills” because their builders thought they looked like a person dressed in a smock; they are utterly charming. When I am standing right beside the one in Water Mill, though, I realize how large it is, and how much power it must have generated when it was allowed to spin.

Then I take a little detour and drive through a wide-open landscape to Sag Harbor, which I find I love instantly. Perhaps that’s because this village, like my own city, was once home to a whaling port more significant than its tiny size would suggest; perhaps it is the way the layers of history blend here, with retro neon signage hanging on the 19th century storefronts along Main Street.

The point of spending 2017 traveling around America is, in part, because I’m afraid I’ll never be able to do it again, and I want to see, if not everything, then as much as I can before that. But already, it is only making me want to travel more. I want to return to Sag Harbor, before I even leave.

Further east, I pass through the village of East Hampton, which strikes me as uncomfortably similar to the town where I grew up, dreaming every minute of escaping, and Amagansett, which looks like the kind of place I imagine no one would ever want to leave. From there, it’s on to Montauk, past the LIRR station and a cluster of commercial necessities, and onto a stretch of road that feels increasingly wild, anticipating Montauk Point State Park. When I stop there and get out of the car, the wind is whipping and I can finally see the lighthouse, red and white, high on a hill. A gate is blocking the path that leads up to it; the lighthouse is closed. I can only stand there, surrounded by seagulls and wind.

When I get back to Orient, towards the end of the day, the place seems even more deserted than it had been in the early morning. I ramble around a bit through empty streets. I know I can’t get lost on the way back to the ferry. All I have to do is drive until the road runs out.

The sun goes down as the ferry plods homewards. The Russians slunk away down the eastern seaboard days ago, and even in darkness, there is no sense that anything more threatening than a strong wind could ever touch us here. As we travel up the river towards the dock, we pass between the old forts built to protect this coast, invisible in the darkness, and the facilities where they make nuclear submarines, their buildings outlined against the night in glittering lights.

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