In 1971, the town decided to open its own high school, and hired architect Theodore Strauss of Katonah, New York to design the building.

The land selected was over one-hundred acres of former farmland and woods located on Gillotti Road, west of Hidden Valley Pond and Meeting House Hill School.

Legend has it that this first cohort wished for the school teams to be named the Seventy-Sixers, to both honor the nation's bicentennial and the first NFHS graduates.

However, the more universal "Rebels" was chosen, the first depiction of which was General David Wooster, a Revolutionary War hero who was mortally wounded at the Battle of Ridgefield after the British raid on Danbury in 1777.

[4] The new school will be located on the same campus as the original building, which will be torn down upon completion of construction, except for the gymnasium, pool, and cafeteria, which will be repurposed for community use.

New Fairfield High School has twenty-four varsity level sports programs, all of which participate in the South West Conference (SWC).

Most home athletic contests take place on the school campus, with facilities including the NFHS gymnasium (basketball, cheerleading, volleyball, wrestling), NFHS Pool (swim & dive), Rebels Stadium (football, cross country, outdoor track), Rebel Turf (field hockey, lacrosse, soccer), and fields for baseball and softball.