Four years after East Hampton Town was founded in 1648, the first mention of the rich soil of Wainscott occurs in official records, citing an order that “a cartway shall be laid out to Wainscott where it may be most convenient.” It wasn’t exactly the LIE, but by 1688 John Osborn arrived, shortly joined by other settlers. Osborns have been farming Wainscott land for more than 10 generations. It is named after a village north of Maidstone, England, an area immortalized in Charles Dickens’ “Great Expectations.”
The Georgica Association, a private group of the well-to-do who built handsome places on large lots at Georgica Pond, established Wainscott’s reputation for style and privacy in the 1890s. The association forced changes in the road patterns to preserve that privacy. During World War II, the association acquired the landmark windmill now on its property off Beach Lane. It had been built in Southampton in 1813, brought to Wainscott in 1852 and then moved to Montauk in 1922 by private interests.