Meet the Head

Diana GleesonIt is my pleasure and honor to welcome you to Bridgton Academy!

I am proud and humbled to have been selected to lead Bridgton Academy as the 49th Head of School. Schools are, and have always been, about students, making schools a fundamentally human enterprise. When I was exploring Bridgton Academy, each interaction with every constituent reinforced for me that I wanted to be part of this unique and impactful school community.

I began my career as a teacher and a coach—learning quickly that trust, fairness, and accountability were cornerstones of creating a community within my team and classroom. Sportsmanship transcends the athletic experience, while hard work, mutual respect, and striving for excellence demonstrate commitment to the community. At the heart of teaching is the responsibility to spark curiosity which leads to deeper engagement and learning. It is clear that Bridgton’s mission and values align with who I am. Community, Curiosity, Sportsmanship, Accountability, and Excellence … I have been living Bridgton’s values my entire career.

Providing a program for young men in a unique, one-year postgraduate environment to prepare for the competitive rigors of college and beyond is different from what other schools do and exactly what young men today need.

Students and families who choose Bridgton know that investing in an additional year of preparation physically, intellectually, and socially in a unique one-year postgraduate environment will provide preparation for the competitive rigors of college and beyond. Bridgton Academy is truly unique in how it emulates a college environment, while simultaneously providing a scaffolding of support and structure that fosters independence and maturity. Bridgton Academy students know and can articulate why they are here—to excel in “The Year That Makes The Difference”.

Come join me in North Bridgton, Maine to experience the transformative experience that is Bridgton Academy.

Go Wolverines!



Diana Gleeson

Diana J. Gleeson

Head of School