Southampton
Southampton was founded in 1640 by settlers from Massachusetts and became a summer colony in the 1870s, three decades before its neighbours — the shingled cottages along the dunes are the original Hamptons architecture. The village keeps a working main street, a whaling-era museum and Coopers Beach, consistently ranked among the best in America, with parking that costs more than dinner.
Why go
The first Hampton — a summer colony from the 1870s, three decades ahead of its neighbours. Shingle-style architecture — the original cottages along the dunes that defined the American beach house. Coopers Beach — regularly ranked the best in the country, with dunes and no development behind it. A real village underneath — founded 1640, with a working main street and a whaling museum.
The character
Southampton was settled in 1640 by colonists from Lynn, Massachusetts, making it the oldest English town in New York State, and it lived on farming, whaling and fishing for two centuries. Its second life began in the 1870s, when New York families started building summer houses on the ocean dunes — the shingle-style cottages that followed, designed by McKim, Mead & White among others, invented the American beach house as a type.
The result is a village with two clocks. Year-round Southampton has a hospital, a college, working farms on the periphery and a main street that sells hardware as well as cashmere; summer Southampton is a social season with charity benefits, hedges cut to the inch and traffic that turns a fifteen-minute drive into an hour. The distinction between it and East Hampton is real to residents and invisible to everyone else: Southampton is older, slightly more formal, and closer to the city by twenty minutes.
Places of character
Coopers Beach — dune-backed ocean beach, wide and clean, with parking that is famously expensive. Southampton History Museum — a 1843 whaling captain's house with outbuildings and a working village setting. Old Halsey House — 1648, the oldest frame house in the state, with a colonial herb garden. Job's Lane and Main Street — the shopping streets, with the Parrish Art Museum's original home on the corner. Shinnecock Hills — the golf course from 1891, one of the five founding clubs of American golf. Sagg Main and Mecox — the potato-field roads north of the ocean, where the Hamptons still look agricultural.
The way to do it
Come on the train or the jitney; the Montauk Highway in July is not worth the car. Cycle the back lanes between the villages — that is where the architecture and the farmland are. Buy a beach pass or go before nine when the attendants are not yet on. And eat from farm stands at least once.
One perfect day
Breakfast at a village bakery, then Coopers Beach early with the sand still cool and the dunes casting shadows. Cycle the back roads north through the potato fields to Sagg and Mecox for the farm stands. Lunch of corn, tomatoes and a lobster roll eaten at a picnic table. Afternoon at the Parrish Art Museum in Water Mill, ten minutes east, in Herzog & de Meuron's long shed of a building. Back to the village for the historical house and Job's Lane. Swim as the beach empties, then dinner early and a drink on a porch with the crickets going.
Grand hotels
The American Hotel, Sag Harbor — 1846 in the neighbouring whaling port, with a wine list of legendary depth. Topping Rose House — a restored 1842 mansion in Bridgehampton, the area's definitive contemporary address.
When to go
Best expression: September, when the ocean is warmest, the crowds have gone and the farm stands peak. Consider: June, before the season proper, with long light and open tables. Avoid if possible: July and August weekends, when Route 27 becomes a car park in both directions.
The frame
Ideal stay 3 nights · Minimum 2 nights · Best arrival train from Penn Station, 2h45 · Airport JFK, 130 km · Walkability the village yes; the beaches by bicycle · Best without a car yes, with a bicycle