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Hamptons and Montauk Travel Guide

One could say the Hamptons mystique began in the late 1800s, when residents of Westhampton Beach and other villages out east began renting rooms to travelers who reached the area first by horse-drawn stage and later on the newly constructed Long Island Rail Road. It wasn't long before the Hamptons had become a resort area of renown, to which affluent city dwellers would escape for cool sea breezes, relaxed country living, and a hefty dose of high society. Today the villages are a curious mix of year-round communities and full-blown summer resorts, drawing vacationers, summer-home owners, and twentysomething "summer share" renters by the carload between Memorial Day and Labor Day. June is still relatively quiet, however, and in May and September you can enjoy pleasant weather while avoiding the peak-season prices and crowds.

Great Itineraries
Pleasures & Pastimes
The North Fork Wine Trail
When to Go

Places to Explore

Amagansett
Bridgehampton
Cutchogue
East Hampton
Fire Island
Greenport
Montauk
Orient
Quogue
Riverhead
Sag Harbor
Shelter Island
Southampton
Southold
Water Mill
Westhampton Beach

Photo: Tana Lee Alves/Shutterstock

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