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Background and history
The hamlet was named after Wainscott, Kent, a village north of Maidstone, England, an area immortalized in Charles Dickens' Great Expectations and from which most of the early settlers of East Hampton came.
The Wainscott School, founded in 1730, was the last public one-room schoolhouse operating in New York until an annex was built in 2008.
Facing the Atlantic Ocean to the south, Wainscott has some of the most expensive property in the world. On its west is the village of Sagaponack, and on the east is the village of East Hampton. Other communities that border Wainscott are the CDPs of East Hampton North and Northwest Harbor to the northeast, the village of Sag Harbor to the north, and the CDPs of Noyack and Bridgehampton to the west (north of Sagaponack).
The east side of Wainscott faces Georgica Pond. The exclusive Georgica Association has a 100-acre (0.40 km2) subdivision on the west side of the pond. The Association's most famous house, called the "Michael Kennedy house" (a lawyer who represented such diverse clients as the Black Panthers and Ivana Trump), was the beach house featured in the 2004 film Eternal Sunshine of the Spotless Mind.
The PBS children's show It's a Big Big World is taped in the industrial park at the East Hampton Airport which is in Wainscott.
The Wainscott railroad station on the Montauk Branch closed in the 1930s.
According to the United States Census Bureau, the CDP has a total area of 7.2 square miles (18.7 km2), of which 6.7 square miles (17.4 km2) is land and 0.50 square miles (1.3 km2), or 6.87%, is water.
It is interesting that Wainscott—such a small town—should present a different landscape than East Hampton or Amagansett. The town is flat: houses border on potato or corn fields that then border on the dune and the ocean. Main Street used to have a General Store and a Post Office. The post office eventually moved to a new building on Montauk Highway and the old post office became a private residence. Before 1935, Main Street was lined with sycamores, but the hurricane took them all down. The day after the hurricane it was posted that free firewood could be had on Main Street, if you were willing to chop it.