The name Amity is derived from both the colonial history of Woodbridge as well as the "friendship" demonstrated among the three founding towns in arranging for a communal educational program.
[7] The residents of the three towns demonstrated their unhappiness by rejecting seventeen proposed budgets during the 2002-3 fiscal year.
[8] In April 2010, Sue Cantin, a former secretary in the school district office, pleaded no contest to misdemeanor charges of embezzling $107,512 in student activity funds.
Current Head Coach Sal Coppola has held the position since 1994 and won his 500th career game in 2022 and holds the all-time CT record for most state championships with 6.
[22] In 2006 the Amity girls' soccer team tied the Class LL state championship with Trumbull High School, after the game went into double overtime and ended with a score of 0–0.
In the 2009–2010 season, the Amity Marching Band went on hiatus, while a new staged performance called Music In Motion was put into a trial production.
This new stage production contained a variety of the Amity Band concepts, including marching, jazz, drumline, colorguard and dance.
In addition, several band members put together an imitation of the dance group Stomp, using push brooms and garbage pails to create a chorus of percussion.
Later in 2008, the department performed the play The Boys Next Door, for which it won the Moss Hart Award for Best High School Production by the New England Theater Conference.
Many parents and students in the Amity community had mixed feelings on the production as it depicts homosexuality, drug use and AIDS.
For that production, Amity received 12 nominations at the 2011 Connecticut High School Musical Theater Awards, but only took home one.
[30] In December 2018, the theater program performed The Curious Incident of the Dog in the Night-Time, featuring an actual Black Labrador.
[30] During the 2019–2020 school year, the program performed the play Dancing At Lugnasa, but the musical The Drowsy Chaperone was cancelled due to coronavirus concerns.
In the 2019–2020 school year, the Amity Debate Team competed in the International Public Policy Forum (IPPF) competition.
[36] In 1980, a three-student team from Amity Regional High School won the championship of the inaugural Connecticut High School Bowl, an academic quiz show produced by New Haven TV station WTNH in association with Albertus Magnus College from 1980 to 1991.
The latest team is best known for participating in the Connecticut version of The Challenge, a quizbowl-type game show courtesy of Cablevision's News 12 Networks.
In May 2009, Amity made it to the state quarterfinals of The Challenge for the first time in school history, but lost to the eventual Connecticut champion, Greens Farms Academy of Westport.