East Hampton
East Hampton was founded in 1648 and made its money from whaling until the artists arrived in the 1870s and the railway brought Manhattan after them; the village green, the windmills and the shingle houses all predate the reputation. Come after Labor Day, when the traffic on Route 27 clears and the beaches at Main and Georgica belong to whoever walks down to them.
Why go
Ocean beaches with no development on them — the dunes are protected and the houses sit behind them. An artists' colony that predates the money — Pollock, Krasner and de Kooning worked here before the hedge funds. A 1648 village green — windmills, a burying ground and shingle houses on Main Street. Farm stands — the Hamptons are still agricultural, and the corn in August is the argument.
The character
East Hampton was settled by farmers from Kent in 1648 and made money from whaling until the 1840s, when the trade moved to New Bedford. What saved it from becoming a backwater was the railway and the painters: by the 1870s artists came for the light on the flat land and the ocean, and by the 1950s Jackson Pollock was working in a barn in Springs, dripping paint on canvas laid on the floor.
The money came later and has never entirely displaced the rest. The village keeps strict controls — no chain signage, tight building rules, and hedges high enough that most of the famous houses are invisible from the road, which is precisely the point. The result is a strange double life: an agricultural town with a 1725 windmill and a farmers' market, and a summer colony where the traffic on Route 27 becomes a national joke each July. Both are real, and September belongs to the first one.
Places of character
Main Beach — consistently rated among the best in America, and free of anything built on it. Pollock-Krasner House, Springs — the barn studio with paint still on the floor; you walk it in slippers. Home Sweet Home Museum — a 1720s saltbox with the windmill behind it, on the village green. Sag Harbor — the old whaling port fifteen minutes north, still working and cheaper. Round Swamp Farm — the farm stand locals queue at; the Hamptons' actual economy for three centuries. Montauk — the end of the island, a lighthouse from 1796, and surf the village side does not have.
The way to do it
Come after Labor Day if you can — the beaches stay warm through September and the traffic vanishes. Take the train or the jitney rather than driving; Route 27 in July is a car park. Cycle between the villages, and shop at farm stands and not restaurants for at least one meal.
One perfect day
Coffee and a walk on Main Beach before eight, when it belongs to dog walkers and the light is flat on the water. Bicycle to Springs for the Pollock house — the studio floor is the most direct encounter with a painter you can have in America. Farm stand lunch: corn, tomatoes, a lobster roll eaten standing up. Afternoon at Sag Harbor for the whaling museum and the harbour. Back for a swim as the beach empties, then a drink on a porch and dinner early, because everything here still runs on a farming clock underneath.
Grand hotels
The Maidstone — a 1750 house on Main Street, Scandinavian-run and the only hotel with the village's own history. Gurney's Montauk — on the ocean at the island's end; the definitive contemporary address on this coast.
When to go
Best expression: September — ocean still warm, crowds gone, farm produce at its peak. Consider: late May, before Memorial Day opens the season. Avoid if possible: July weekends, when the road from New York takes four hours for a hundred miles.
The frame
Ideal stay 3 nights · Minimum 2 nights · Best arrival the train from Penn Station, 3 hours · Airport JFK, 160 km · Walkability the village yes, the beaches by bicycle · Best without a car yes, with a bicycle