Chimney Company in New Fairfield, CT

In pre-colonial times, the indigenous people of New Fairfield were part of an alliance of tribes that extended from the source of the Housatonic to the sea.

In 1724, colonial settlers from Fairfield, Connecticut, received approval from the General Assembly of the Colony of Connecticut to establish a new township. According to one account, they negotiated with Chief Squantz of the Schaghticoke tribe of Algonquian lineage. Alternatively, it is told that they did not negotiate with Chief Squantz because he moved to the north end of Squantz Pond land area and refused to “sell” the township of New Fairfield. They returned in the Spring of 1725, but found that Chief Squantz had died during the winter. His four sons and heirs refused to sign the deeds. It was not until four years later that the white men called “The Proprietors” finally got the drawn marks of several other native people who may not have had authority to sell the land. They “purchased” a 31,000-acre (13,000 ha) tract of land that is now New Fairfield and Sherman, for the equivalent of about 300 dollars, and on April 24, 1729, the deed was recorded on May 9, 1729, and is now deposited in the archives of the state capital in Hartford, Connecticut.

Settlers originally spelled the town as “Newfairfield”. It started as a very small farming community, and was not incorporated as a town until 1740. The town of Sherman separated from New Fairfield in 1862, as the size of the combined towns made it difficult to travel to church.