Canty was involved in several high-profile free speech disputes with students before transferring to the Board of Education for two years and then announcing his departure from the school district in 2013.

In 1940, a town meeting approved the purchase of the Harbs Farm property, a 65-acre (260,000 m2) tract near the intersection of School and Danbury Roads.

Although this was a new facility, it was quickly deemed inappropriate due to its small size, in the wake of the "baby boomer" education era.

[13] The present day Wilton High School opened in September 1971, reaching a maximum student population of 1,646 during the 1976-77 academic year.

The project included new classrooms, more modern science laboratories, new music rooms, a larger cafeteria and a new theater building with an 800-seat auditorium.

An investigation by the Wilton Bulletin in 2006 found that the high school "safe room" had never been inspected by the fire marshal and lacked a Building Department certificate of occupancy.

[20] Maryanne Lombardi made similar claims that her 9-year old autistic son, who did not speak, was routinely sent to a "padded cell called the timeout room" at another Wilton school.

[19][20] Gloria Bass, the grandmother of two special needs students, also said that one child had been restrained for months in a storage closet without her knowledge.

He justified his action by claiming it might hurt Wilton families "who had lost loved ones or who had individuals serving as we speak," and that there was not enough classroom and rehearsal time to ensure it would provide "a legitimate instructional experience for our students.

"[21] The play, Voices in Conflict, had been written and produced by students under the direction of Bonnie Dickinson, a Theatre teacher with 13 years' experience.

School officials, including Superintendent Gary Richards, notwithstanding national attention over the cancellation and a letter protesting signed by Stephen Sondheim, Edward Albee, Christopher Durang, John Guare and John Patrick Shanley, refused to allow the production to be performed at the school.

Superintendent Kevin J. Smith said the ban was made to remove distractions in classrooms, promote face-to-face interaction between students, improve mental health and decrease cyberbullying and other disruptive online behavior.

Students who opposed the ban were mostly concerned with the "unrealistic" standards made by the school, not the belief that cell phone use disrupts learning.

Student Sophia Gordon, commenting on the ban's goal on increasing social interaction, said "You can't force people to be friends.