Cheshire Academy has solidified itself as a top New England program in recent years, most recently hosting the NEPSAC Class B title game in 2023. In prior years, the Cats have won multiple league championships as well.

Cheshire Academy has recently placed players at all collegiate levels. The Cats play a competitive schedule against some of the top teams in the region and kick off the year with a preseason trip in March to Orlando, Florida. The program draws student-athletes looking to play at the next level, but also those students who want to try a new sport. Games are played on a new turf field and student-athletes also have access to an indoor drop-down batting cage inside Arthur Sheriff Field House in the off-season.