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.

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.

[3] 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.

[4] In 1926, Connecticut Light and Power (CL&P) began construction on Candlewood Lake, considered by many to be an engineering wonder.

CL&P flooded the valley to control the water flow from the Housatonic and Rocky Rivers and produce hydroelectric power for the region.

Candlewood Lake was named for the Native American practice of using stripped wood from pine trees as kindling for fire.

The lake shares its shores with the towns of New Fairfield, Sherman, New Milford, Brookfield, and Danbury.

New Fairfield borders Danbury to the south, Brookfield to the southeast, New Milford to the northeast, Sherman to the north, and Patterson, New York to the west.

Once a summer resort destination, the lake shore within New Fairfield is now mostly populated with many year-round homes.

The 2000 census reported that New Fairfield was the most heavily Irish-American community in Connecticut, with about 32% of the residents claiming Irish ancestry.

Lyndon B. Johnson is the only Democrat who has managed to win the town in his landslide victory in 1964.

Housatonic Area Regional Transit (HART) operates a weekday commuter shuttle between Southeast station, and the town's two park and ride lots (located at the Ball Pond Firehouse and the Company A Firehouse).