The Hamptons: America’s Original Summer Colony

Aug 1, 2022 by Capt. Jeff Werner

This celebrity-sighting minefield is famous for everything, right down to its cookies.

Long before Andy Warhol, Paul McCartney, Jerry Seinfeld, Christie Brinkley, Gwyneth Paltrow, Kurt Vonnegut, and Truman Capote bought homes in the Hamptons, the indigenous Shinnecock and Montaukett tribes lived there. The Shinnecock are the most well-known, as they were sailors and fishermen, and their tribesmen served aboard the whaling ships that called Sag Harbor home during the late 1800s.

The Hamptons lie along the South Fork of the eastern end of Long Island, New York, between Montauk Point and the Moriches, and are comprised of two dozen villages and hamlets. The most well-known destinations of this seaside resort area are Montauk, East Hampton, Sag Harbor, Southhampton, Shinnecock Hills, Quogue, and Westhampton. Of course, there is a Northhampton. It can be a bit confusing to the first-time visitor since Westhampton and Northhampton are legally part of the town of Southhampton.

When the Long Island Rail Road made its way 90 miles east of New York City to Bridgehampton in 1870, well-to-do Manhattanites traded the city’s summer heat for the Atlantic shoreline’s cool breezes. The Springs of East Hampton developed into an artist colony after the painter Jackson Pollock purchased a house and barn there in 1945, with the down payment loaned by art patron Peggy Guggenheim. In addition to artists, the Hamptons have been synonymous with “truck farms,” where farmers raise vegetables for local markets. Many vegetable farms are still active in the Hamptons, although it is more well-known as wine country. There are more than 60 vineyards and wineries in the Hamptons and over on the North Fork.

Here’s a bucket list of 28 things you must do when in the Hamptons.


All harbors, anchorages, and marinas in the Hamptons are most easily accessed by cruising between the North Fork and the South Fork that make up the Fishtail at the eastern tip of Long Island. Whether entering the Fishtail from Long Island Sound or from Block Island Sound, spend some time planning your cruise by reviewing the charts of Lake Montauk, Gardiners Bay, Threemile Harbor, Sag Harbor Bay, Little and Great Peconic Bays, Shinnecock Bay, and the Shinnecock Canal. It is possible to enter the Fishtail through Shinnecock Inlet from the Atlantic Ocean, but the U.S. Coast Pilot advises: “The inlet should not be attempted without local knowledge because of the frequent changes in channel depth” and “tidal currents through the inlet can be dangerous; caution is advised.”