The Cheshire Academy baseball program has become one of the top prep school programs in the region. The Cats compete in the Western New England Prep Baseball League and have won multiple league titles in recent years. In addition, many student-athletes go on to play baseball at the collegiate level.

The season opens with a spring break 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 in the off-season.