Cheshire High School is a comprehensive public high school serving approximately 1,538 students; it is the sole comprehensive high school of Cheshire Public Schools. Located at 525 South Main Street in Cheshire, Connecticut, Cheshire High School is 15 miles (24 km) north of New Haven and 25 mi south of Hartford. It is the town's sole public high school. As of 2016, Cheshire High School has approximately 1,538 students, 104 faculty members, six guidance counselors, three assistant principals, and one principal. The school is accredited by the New England Association of Secondary Schools and Colleges.

Renovations

The last renovations to Cheshire High School were completed during the summer of 2000. Prior to this, the school was last renovated in 1971. Designed by DeCarlo & Doll, Inc. and built by Trataros Construction, Inc., the renovations added 73400 sqft of space at a cost of over eight million dollars. The renovation brought to the school a new two-story wing of about 51000 sqft, containing: A new band room was also built in the rear of the building. Additionally, three science classrooms were renovated, faculty parking lots were created, and landscaping work was done in the front of school, around the new wing. As this new addition faced the main road, it became the new facade and main entrance to the school. Previously, the main entrance was tucked away at the south side of the building. In 2011, the Technology Department received a $73,000 grant to improve its video studio. Cheshire High School offers multiple media-based classes which use the studio, including video production and news media production. Graduates had been excelling at media colleges for years prior to the renovation and now are doing so to a greater extent.

Athletics

Cheshire High School participates in the Southern Connecticut Conference.

Baseball

The Rams baseball team won the class LL state championship in 2018.

Softball

The Rams softball team won their first class LL state championship in 2016 during their first ever unbeaten season finishing 27-0.

Arts

The Ram Band marched in parades such as the 43rd Presidential Inaugural Parade, the 1999 Tournament of Roses Parade, and the 2000 Macy's Thanksgiving Day Parade. Cheshire's Winter Percussion Ensemble won first place two years in a row (2008–09) at MAC Championships. They also won USSBA National Championships in the AAA category in 2011.

Notable alumni