Cheshire Academy has solidified itself as a perennial New England power in recent years. The Cats have reached the Western New England Prep Softball Association title game each season dating back to 2012, and won the last three Class B championships.
Cheshire Academy has recently placed players at Division I, II and III college programs including Hofstra University, Keene State and others. 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. Student-athletes also have access to an indoor drop-down batting cage inside Arthur Sheriff Field House.