The Hamptons Have Been New York's Old-Money Summer Address Since the 1870s

The Hamptons is not one town but a string of villages and hamlets along Long Island's South Fork, roughly two to three hours from Manhattan depending on traffic and the day of the week. Southampton, East Hampton, Sag Harbor, Bridgehampton, Water Mill and Montauk each have a distinct character, but together they have formed New York's default summer retreat for the wealthy since well before the private-jet era made the commute easy.

A retreat that predates the Gilded Age crowd

Southampton, settled by English colonists in 1640, is among the oldest English settlements in New York State, but its shift toward a summer resort for wealthy New Yorkers began in the 1870s and 1880s, as rail links from Manhattan improved and old farming and whaling families' land began attracting outside buyers. Shinnecock Hills Golf Club, founded in Southampton in 1891, was one of five founding member clubs of the United States Golf Association in 1894, giving the area an institutional claim to old-money status that has outlasted most of the original Gilded Age cottages themselves.

Windmills, not mansions, are the oldest landmarks

Several of the Hamptons' most recognisable structures predate the resort era entirely. The Hayground Windmill in Bridgehampton and similar mills scattered through East Hampton and Water Mill date to the 18th and 19th centuries, built for the area's original farming economy, and have since become local landmarks in a landscape now dominated by hedged estate driveways rather than working farms.

Montauk as the quieter edge

At the South Fork's easternmost point, Montauk has kept a rougher, more working fishing-village character than Southampton or East Hampton, though it has drawn its own wave of newer money and boutique hotel openings in the past decade. Hither Hills State Park, just west of the town, remains one of the more undeveloped stretches of coastline on the entire South Fork.

Traveller tips

• East Hampton Airport and a Long Island Rail Road line from Manhattan's Penn Station both serve the area; summer weekend traffic on Route 27 can add hours to a road trip.
• July and August are peak season and heavily booked; late spring and early autumn offer a quieter, cheaper alternative with largely similar weather.
• Beach access in parts of Southampton and East Hampton is restricted to residents or permit holders; Hither Hills and several Montauk beaches remain open to all visitors.
• Sag Harbor's compact former whaling village centre is a walkable alternative to the more spread-out estate areas nearby.