Hamptons and Montauk

Hamptons and Montauk Travel Guide

New York's Long Island is the largest island on America's East Coast -- 1,682 square miles total. It extends 120 miles eastward from New York City, traversed by the notoriously clogged Long Island Expressway (LIE, or I-495) and encompassing two New York City boroughs (Brooklyn and Queens), congested commuter towns, the farmland of the North Fork, and the world-famous summer resorts of the Hamptons and Montauk on the South Fork.

The seaside villages of the Hamptons, some dating from the 1600s, stretch west to east from Westhampton Beach to Amagansett; at the tip is the fishing community of Montauk. Both locals and the omnipresent rich and famous summer here, and they all come for what's possibly the nation's finest stretch of white-sand beach. Rolling farmland and vineyards, spectacular mansions and ranches, and blue skies and sunshine add to the allure.

One could say that the "Hampton mystique" began in Westhampton Beach. In 1870, residents began renting out rooms to travelers who reached the area on the newly constructed Long Island Railroad. Soon the practice spread and it was not long before the Hamptons had become a resort area of renown. Today the Hamptons are full-blown summer resorts, drawing vacationers, summer-home owners, and twentysomething "summer share" renters out east by the carload between Memorial and Labor days.

Just east of Westhampton Beach, Quogue and East Quogue are considered part of the Greater Westhampton area. Quogue's stately Victorians are nestled along tree-lined streets, and contemporary mansions line the ocean along Dune Road. In East Quogue, acres of farmland and pine forest, as well as beautiful bay and ocean beaches, are enlivened by Main Street shopping and lively nightlife.

The town of Southampton was established in 1640 by English colonists and was the first settlement in New York State. With its Historical Museum, Southampton has a decidedly Colonial feel, and its Job Lane's shopping district oozes chic. Windsurfers enjoy three bays: Peconic, Noyac, and Shinnecock (which is also a popular diving spot).

The farming community of Water Mill is the nation's only community with a functional, working water mill and windmill. Elegant Bridgehampton, just east of Water Mill, has antiques shops, art galleries, and restaurants in which you can sip wine made from grapes grown in local vineyards. This is also horse country, and Bridgehampton is home to the prestigious annual Hampton Classic Horse Show and the Mercedes-Benz Polo Challenge.

The pearl of the Hamptons, East Hampton was founded by farmers in 1648, and farming remained its main source of livelihood until the 1800s, when the town began to develop into a fashionable resort. East Hampton's considerable wealth and Puritan heritage now combine into a particularly understated prosperity, and much of the village remains as it was during the 18th century. Amagansett is a Native American word meaning "place of good water," and from its earliest beginnings, the town has possessed a tranquility that is perfectly suited to fishing and offshore whaling.

At the easternmost part of the island, Montauk doesn't put on any airs, with its seaside hotels, thriving fishing and boating community, and surfer-studded beaches. The Montauk Point Lighthouse is the oldest operating lighthouse in the state and the fourth oldest in the country.

The North Fork, across the Great Peconic Bay from the Hamptons and the South Fork, is best known for its quiet villages, bountiful farm stands, and burgeoning wine industry. New England-style hamlets such as Jamesport, Cutchogue, and Southold are peppered with unpretentious restaurants and interestings shops that seems transported from another era. Clean, uncrowded beaches lie to the south on Great Peconic Bay and to the north on Long Island Sound.

Shelter Island lies between Long Island's North and South forks. Reachable only by boat (there's regular ferry service), the 11 1/2-square-mi island offers at least a partial escape from the summer traffic and crowd snarls of the Hamptons. Quiet country lanes wind across the island's rolling land, nearly a third of which has been set aside as a nature preserve that's a bird-watcher's delight.