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The population was 43, at the census, making it the second largest village in New York by population. A settlement since the s, it was once an oystering community and later a resort popular with the New York City theater community.
Before people of European ancestry came to the area, the land was part of the territory of the Meroke Indians. In , residents voted to rename the village Freeport, adopting a variant of a nickname used by ship captains during colonial times because they were not charged customs duties to land their cargo. After the Civil War , Freeport became a center for commercial oystering. This trade began to decline as early as the beginning of the 20th century because of changing salinity and increased pollution in Great South Bay.
From , Freeport was served by the Southside Railroad , which was a major boon to development. The most prominent figure in this boom was developer John J. Randall ; among his other contributions to the shape of Freeport today were several canals, including the Woodcleft Canal, one side of which is now the site of the "Nautical Mile".
In the years after incorporation, Freeport was a tourist and sportsman's destination for its boating and fishing. The ferries took people to Point Lookout , about three miles 5 km south of Freeport, where there is an ocean beach. In the late 19th century, Freeport was the summer resort of wealthy politicians, publishers, and so forth.
