Cheshire Academy student-athletes have gone on to play at Vanderbilt, Dartmouth, Trinity and many other college programs. The Cats have become one of the top prep school programs in the region, winning the Western New England Prep Baseball League championship twice since 2015.
The Cats play a competitive schedule against some of the top teams including The Frederick Gunn School, Salisbury, Suffield Academy and others. The season opens with a trip in March to Orlando, Florida. Cheshire Academy plays its home games at Alumni Field and student-athletes also have access to an indoor drop-down batting cage.