Montauk

Montauk sits at the tip of Long Island's South Fork, which means it has water on three sides and one road in. Highway 27 ends here, at the lighthouse that George Washington commissioned in 1792, and the town has arranged itself in the twenty miles before that terminus — fishing harbour, a few streets of shops and restaurants, the bluffs running east, and the beaches stretching in both directions. Ditch Plains, on the Atlantic-facing southern shore, is the break that everything else in Montauk is organised around for a certain kind of visitor. It's a consistent beach break, NW and NE groundswells turning into rideable walls across a sandy bottom, the water cold and the lineups manageable outside July and August. The East Coast doesn't produce surf towns in the way the West Coast does — the Atlantic is less consistent, the culture more seasonal — but Montauk is the closest thing to one, and Ditch Plains is the reason.

The town itself operates on two registers. From Memorial Day to Labor Day, it runs at full volume — the Hamptons crowd arriving from the west, the surf crowd already there, live music at the Surf Lodge, restaurants booked weeks in advance. From September through May, the population drops, the prices follow, and what's left is a stripped-back version of itself that the locals prefer and the avid surfer understands: cold water, long swells, empty lineups, and the lighthouse visible from the water on a clear day. The best hotel rooms on the block are fifty metres from the sand. All five hotels on the strip are there because someone understood that Montauk needed a different kind of hotel than the Hamptons.