Since 2019 over 50 players have moved on from The Winchendon School to playing in college.
Alumni in College: Bates College, Bentley College, Clark University, Colby College, University of Dayton, Gardner Webb University, Georgetown University, Hamilton College, The College of the Holy Cross, Merrimack College, Northeastern University, Rollins College, Saint Anselm College, St. Lawrence University, Tufts University, University of Maine, University of Massachusetts – Amherst and Lowell, Wesleyan University, and more. The 2019 team also featured a New York Yankee (MLB) draft choice.
The Winchendon School baseball program is led by Head Coach John Toffey. In his first season as Head Coach at Winchendon the team had a 20-6 overall record and won its first-ever New England championship. Coach Toffey has seen over 75 of his former student-athletes complete in college at schools such as Bates, Clark, Colby College, Dayton, Gardner Webb, Georgetown, Hamilton College, Holy Cross, Maine, Merrimack, Northeastern University, Rollins College, Saint Anselm, St. Lawrence, Tufts, UMass-Amherst, UMass-Lowell, Wesleyan, Vanderbilt ( All American), Clemson, Richmond, Maine, Boston College ( All American), Northeastern, Dartmouth ( All IVY League), University of Pennsylvania ( Ivy League Player of the Year), Bentley ( MLB draft choice), Hartford, Michigan, Tufts, UCONN, Tulane, and many more. He has coached 7 MLB draft choices including two top 5 rounds selections- NY Yankees-3rd and Oakland Athletics-4th. The 2019 team featured a New York Yankee (MLB) draft choice and the 2021 team had 19 student/ athletes move on to play college baseball. In addition to his coaching responsibilities, Toffey is the Dean of Enrollment Management at The Winchendon School.
Coach Toffey is assisted by John Brickley who has coaching experience at the high school, college, and professional level. Coach Brickley is a long time MLB scout working for the Toronto Blue Jays and Cincinnati Reds. He has also managed in the Cape Cod Baseball League.
Our Head Athletic Trainer is Jon Harris– widely considered one of the top Athletic Trainers in New England.
Our Head Strength and Conditioning Coach is Bryan Muenzner.