An Insider’s Guide to a Smarter East Hampton Weekend, With the Right Detours

The Hamptons has been synonymous with summer since the Long Island Rail Road first reached the South Fork in the 1870s, when New York’s wealthiest families began building vacation cottages along the dunes of Southampton and East Hampton. Artists followed a few decades later, and by the mid-20th century, the potato fields of Springs had quietly become ground zero for Abstract Expressionism, with Jackson Pollock and Lee Krasner working a few miles from where financiers now summer. 

That mix has never really gone away, and neither has the crowd. Nearly a century and a half after the first grand houses went up, New Yorkers still flock to the Hamptons every June for the start of summer. Increasingly, though, it doesn’t empty back out after Labor Day. Restaurants that once shuttered for the season are staying open into the winter, hotels are extending their calendars, and a place built on summer has slowly become a place people visit and live nearly year-round.

From Southampton to Montauk is a span of roughly 30 to 35 miles, but despite its relatively small size, getting from one town to another can take quite a while, particularly during the summer—traffic simply crawls. For those posting up in the stretch from East Hampton through Montauk, this is the territory worth knowing well. A couple of picks sit farther afield, including a French bistro in a Southampton hotel and a lake house-style resort across the bay on Shelter Island, worth the extra half-hour, or on the way back to the city. Here’s where to stay, where to eat and what’s worth knowing long past the summer season.