Designed by DeCarlo & Doll, Inc. and built by Trataros Construction, Inc., the renovations added 73,400 square feet (6,820 m2) of space at a cost of over eight million dollars.

[4] The renovation brought to the school a new two-story wing of about 51,000 square feet (4,700 m2),[4] 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.

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

Cheshire's Winter Percussion Ensemble won first place two years in a row (2008–09) at MAC Championships.