The Hamptons have been synonymous with summer since the Long Island Railroad first reached the South Fork in the 1870s, when New York’s wealthiest families began building vacation homes along the Southampton and East Hampton dunes. Artists followed a few decades later, and by the mid-20th century, the Springs potato fields had quietly become ground zero for Abstract Expressionism, with Jackson Pollock and Lee Krasner working miles from where financiers now summer.
That mix has never gone away, and neither has the crowd. Nearly a century and a half after the first stately homes were erected, New Yorkers still flock to the Hamptons each June for the start of summer. Increasingly, however, it does not empty after Labor Day. Restaurants that used to close for the season are staying open during the winterhotels are expanding their calendars and a place built in summer has slowly become a place people visit and live almost all year round.
Southampton to Montauk is roughly 30 to 35 miles, but despite its relatively small size, getting from one town to another can take quite a while, especially in the summer – the traffic just drags. For those posting in the stretch from East Hampton to Montauk, this is territory well worth getting to know. A few choices lie further afield, including a French bistro in a hotel in Southampton and a lake-style resort along the bay on Shelter Island, worth the extra half hour or so on the way back to the city. Here’s where to stay, where to eat and what’s worth knowing during the summer season.
