Late fall on North Main Street in East Hampton. The summer crowd is gone, and Hook Windmill has the street to itself.

Say “the Hamptons” in Manhattan and people picture one place. The Hamptons are a string of villages and hamlets on the South Fork of Long Island, each with its own history and its own clubs.

Old money shaped the map early, though never neatly. Southampton became the society colony. East Hampton became the painters’ village. Both drew artists and the rich, but each kept its own flavor.

The Map: Two Towns, Many Villages

The Hamptons sit inside two towns, Southampton and East Hampton. Each town holds a cluster of villages and hamlets.

  • Town of Southampton: Westhampton Beach, Quogue, Hampton Bays, Southampton Village, Bridgehampton, Sagaponack and part of Sag Harbor.
  • Town of East Hampton: East Hampton Village, Amagansett, Springs, Wainscott and Montauk.

The names matter. A house “in Southampton” can mean the village or the whole town, and locals hear the difference right away.

How to Get to the Hamptons

The Hamptons start roughly 90 miles east of Manhattan. Most drivers take the Long Island Expressway east, leave at Exit 70, and pick up Route 27, the road that runs through the villages.

Without traffic, the drive takes about two to three hours. On a summer Friday it can easily double. That is why weekenders try to leave the city before 1 p.m. or after 9 p.m. Others book a Manhattan to Hamptons car service and spend the ride working, or sleeping, in the back seat.

There are other ways out. The Long Island Rail Road runs its Montauk Branch from Penn Station, with more trains in summer. The Hampton Jitney picks up at several stops in Manhattan. Helicopters and seaplanes make the trip in under an hour.

Flying In to JFK

Guests flying in from Europe for a Hamptons weekend often land at JFK, in Queens. The airport sits east of Manhattan, so the drive out skips the city.

After a long flight, a taxi line with three suitcases is hard work. A JFK airport car service can track the flight, meet guests at arrivals and head straight east. Before booking, ask whether waiting time is included if the flight lands late.

Southampton: Where It Started

Southampton is where the colonial story on the South Fork begins. Settlers landed at Conscience Point in 1640, and the village grew from there.

The summer people came in the 1870s. Wealthy New Yorkers built cottages near the ocean, and by 1882 the village had about 30 summer homes. A group led by the doctor T. Gaillard Thomas called themselves the Southampton Summer Colony. Thomas and his circle are credited with starting Shinnecock Hills, the Meadow Club, the Southampton Beach Club and St. Andrew’s Dune Church.

Shinnecock Hills Golf Club was founded in 1891. Its clubhouse, designed by McKim, Mead & White, opened in 1892, and the club calls it the oldest golf clubhouse in the country. The course has hosted the U.S. Open six times, most recently in June 2026. Painters came too. From 1891 to 1902, William Merritt Chase ran the Shinnecock Hills Summer School of Art nearby.

The Shinnecock Hills Golf Club clubhouse, on its hill in Southampton since 1892

Back in the village, stop at the Southampton Arts Center on Jobs Lane. The building was the first home of the Parrish Art Museum, which Samuel Longstreth Parrish founded in 1898.

Water Mill and Bridgehampton: Art and Horses

Head east and the hedges give way to open fields. In 2012 the Parrish Art Museum left Jobs Lane for a new building in Water Mill, designed by Herzog & de Meuron, the Pritzker Prize-winning firm.

The Parrish Art Museum in Water Mill, its home since 2012

Bridgehampton belongs to the horse set. The Hampton Classic has held its show on the same Bridgehampton grounds since 1982. It runs for eight days each August and ends with Grand Prix Sunday, the week many families treat as the close of summer.

Sag Harbor: The Old Whaling Port

Sag Harbor sits in both towns, split along Division Street. In 1789 it became one of the first official ports of entry in the United States. Whaling made it rich, and the trade peaked in the 1840s.

The Sag Harbor Whaling Museum fills an 1845 Greek Revival house built for a whaling merchant. Down on Long Wharf, the boats now carry weekend sailors, not whale oil.

Boats along Long Wharf in Sag Harbor, once a busy whaling port

East Hampton: Shingles, Privet and a Windmill

Puritan farmers founded East Hampton in 1648, and the village has kept its bones. Walk up North Main Street to Hook Windmill, built in 1806 by Nathaniel Dominy V, a local craftsman. The mill is listed on the National Register of Historic Places and sits inside the North Main Street Historic District.

East Hampton drew painters early. In the late 1870s, members of New York’s Tile Club came out to paint the East End. In 1884 Thomas Moran and his wife, the etcher Mary Nimmo Moran, finished a studio at 229 Main Street. The Moran Studio opened to the public in 2018.

Closer to the ocean is the Maidstone Club, a private club that dates to the 1890s. Its golf holes wind around Hook Pond, the dunes and the beach grass.

Springs: The Artists’ Corner

The painters kept coming. In November 1945, Jackson Pollock and Lee Krasner moved into a farmhouse in Springs, a hamlet in East Hampton. Pollock started working in the barn out back the next year.

Today the Pollock-Krasner House and Study Center belongs to the Stony Brook Foundation and has been a National Historic Landmark since 1994. When conservators lifted the boards Pollock had laid over the barn floor, they found the original floor still covered in his paint.

Montauk: The End of the Road

Keep driving east on Route 27 and the land runs out at Montauk Point. The lighthouse there was authorized in 1792 under President George Washington and finished in 1796, the first lighthouse built in New York State.

The Montauk Historical Society runs it as a museum. The rest of Montauk runs on boats and boards. It has the largest commercial and recreational fishing fleet in New York State, and surfers paddle out at Ditch Plains. The town markets itself as “The End.”

Southampton vs East Hampton: Which to Pick

It is the first thing newcomers ask. The two villages grew up around different crowds, and the difference still shows.

  • Choose Southampton for the society side: the old summer colony clubs, Shinnecock Hills and Coopers Beach, which Dr. Beach named the best beach in the country in 2010 and again in 2025. It is also an easy base for Water Mill and Bridgehampton.
  • Choose East Hampton for the artists’ side: Hook Windmill, the Moran Studio on Main Street and the Pollock-Krasner House in Springs. Main Beach made the same 2025 top 10 list, at No. 5, and Amagansett and Montauk sit just to the east.
  • Choose Sag Harbor for the boats on Long Wharf, the Whaling Museum and a village that belongs to both towns at once.

The Quiet Months

For a long weekend out east in the off-season, some families book one car and driver for the whole trip, out and back. Companies such as Gotham Ride Chauffeur Service, a New York operator since 2010, handle that kind of booking.

Summer gets the headlines. Come in November, after the crowds, and you get the windmill, the wharf and the lighthouse almost to yourself.