John J. Toffey VI

Mr. Toffey is entering his 7th year of service at The Winchendon School. In his current role as The Assistant Head of School, Mr. Toffey overseas enrollment management, our co curricular programs, and strategic initiatives for the school. As a graduate of the Isenberg School of Management at UMass-Amherst and the St. Sebastian’s School in Needham, Mr. Toffey is continuing to pursue his education. He most recently earned his Masters degree in Independent School Leadership from Vanderbilt University. Prior to his time at Winchendon, Mr. Toffey worked at two schools in Connecticut. The Salisbury School (7 years) and Cheshire Academy (3 years).

Additionally, Mr. Toffey serves on the board of The Applewild School in Fitchburg, Massachusetts and the North Central Sting youth hockey program. He is a well known athletic coach, having led multiple teams to New England Championships and earning national recognition. Mr. Toffey is often featured in the New England Baseball Journal as one of the most prominent figures in New England baseball. The Winchendon School completed a state of the art multi-purpose turf athletic complex in the fall of 2022, which Mr. Toffey now uses as he coaches The Winchendon School’s Baseball teams. In his free time Mr. Toffey enjoys coaching his children’s youth sports, reading, cooking, and skiing (he is still the beginner in the family).

The Toffey family is proud to call The Winchendon School home. John’s wife, Jessica Toffey, works as the Director of The Hatch Center and the Associate Director of Admissions at the School. Their children Jack (8), Lola (6), and Tobin (4), all attend The Applewild School. You can often see the Toffey family cheering on our Winchendon School students around campus, in the theatre, the ice rink, and on the playing fields! When school is not in session the Toffey family calls Cape Cod home.