When the summer visitors have gone home, the Hamptons on Long Island become what they originally were: farming villages, whaling harbours and a long Atlantic beach. Our route follows Montauk Highway eastward, from the oldest English settlement in New York State to the lighthouse at the very tip of the point.
The Hamptons is the collective name for the coastal communities on Long Island's South Fork, in the townships of Southampton and East Hampton in Suffolk County. The area stretches from Westhampton in the west to Montauk in the east, with the Atlantic to the south and bays such as Shinnecock Bay and Gardiners Bay to the north. In the summer, the population grows considerably; in the winter, it shrinks again. It is this seasonal rhythm that makes autumn the best time to see the villages as they really are – with farms and vineyards still in operation.
The villages have early ties to the New England coast, particularly Connecticut, and several of them are planned as New England towns. It was the railway from New York in the late 1800s that turned them into a summer colony. The route below follows the same direction, eastward.
Southampton – where it all began in 1640
On 12 June 1640, a group of English settlers from Lynn in Massachusetts landed at what is today called Conscience Point. Southampton is the oldest English settlement in the state of New York and takes its name from the Earl of Southampton. The Shinnecock people helped the settlers with land and knowledge of maize, shellfish and fishing; the Shinnecock Reservation, established in 1701, is one of the oldest in the USA. Halsey House on Main Street, dating from 1660, is counted among the oldest timber houses of English type in the state.
The summer colony has a founder. The New York-based doctor Theodore Gaillard Thomas began in 1863 to convince his wealthy patients of the healthy country air, and he and his circles founded St. Andrew's Dune Church, Shinnecock Golf Club, Meadow Club and Southampton Beach Club. Today, the most expensive houses are located in the southern part of the village, the Estate Section, and along the coastal roads Gin Lane and Meadow Lane – the latter known as Billionaire Lane.
Just north of the village lies Shinnecock Hills Golf Club, which has hosted the US Open six times, most recently in 2026 and for the first time as early as 1896.
Water Mill – art moves out into the fields
The next stop is the Parrish Art Museum in Water Mill. The museum was founded in 1898 by the lawyer Samuel Longstreth Parrish in Southampton, and in 2012 it moved to a low, barn-like building designed by Herzog & de Meuron. The collection comprises more than 3,500 works and focuses on artists from Long Island's art colonies – Jackson Pollock, Lee Krasner, Willem de Kooning and Roy Lichtenstein. The museum holds one of the world's most important collections of the Impressionist William Merritt Chase, who founded a summer art school in Shinnecock Hills, as well as of the realist Fairfield Porter.
East Hampton – windmills and shingle houses
East Hampton was founded in 1648 by Puritan farmers and was first called Maidstone. Without a good harbour, the village lived off farming and stranded whale. When the railway reached Bridgehampton in 1870, summer visitors began to arrive, first to guesthouses on Main Street and then to "cottages" that were sometimes entire estates. The Shingle style dominated from the 1880s, and in 1895 the Montauk Branch was extended through East Hampton to Montauk. Most of the great estates were built in the 1910s and 20s.
The windmills attracted painters as early as the 1890s, and by the mid-20th century the area had become an artists' colony for the abstract expressionists. By Georgica Pond lies Grey Gardens, the house from 1897 where Edith Bouvier Beale and her daughter – aunt and cousin to Jacqueline Kennedy Onassis – lived for decades, and which gave its name to the Maysles brothers' documentary from 1975. The house was sold in 1979 and restored.
Sag Harbor – the whaling harbour
Head north to Sag Harbor on Gardiners Bay. The village was one of the great whaling ports of the 19th century, and in 1789 it reportedly had more tonnage of rigged vessels in trade than New York, according to contemporary accounts. That same year it was designated the United States' first official customs port, and the customs house was the first on Long Island. The entire business district is today a protected historic district, with the Old Whaler's Church, a whaling museum and the customs house along Main Street. The boundary between Southampton and East Hampton runs straight through the village, along Division Street.
Montauk – the lighthouse furthest out
The final stretch follows Montauk Highway out to Long Island's easternmost point. Montauk Point Light was approved by Congress under President George Washington in 1792 and built in 1796 – the new USA's first public building project. It was New York State's first lighthouse and is the fourth oldest active one in the USA. The tower was built up to its current height of 33.68 metres in the 1860s, and the brown band was added in 1899.
The lighthouse is run as a private museum by the Montauk Historical Society and has been a National Historic Landmark since 2012. During the Second World War, the army took over the area, and the gun emplacements at Camp Hero are still visible. In October light, without the summer traffic, it is one of the most beautiful places on the entire East Coast to end a day.
Property data for the area can be found in VERA PI's guides to East Hampton, Southampton and Suffolk County. More destinations can be found among Metro Mode's destinations.
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