MEET OUR HEAD OF SCHOOL

Tom Woelper

A Message from the Head of School

What drew me to Cheshire Academy — and what I believe will draw you here — is a school that has never mistaken sameness for excellence. Since 1794, we have built our education around the individual student: who they are, what they need, and who they are becoming. Our mission says it plainly.

Cheshire Academy challenges and supports individual students in developing the character, critical thinking, and confidence to flourish as purposeful global citizens.

Individual growth, in service of global purpose. That is the work.

Step onto our historic 104-acre campus and you will find a genuinely global community — students from across the country and around the world learning alongside one another every day. The diversity is not the accomplishment in itself; what we do with it is. Students here learn to work across difference because they live it, in classrooms and dormitories, on fields and stages, and at the dining hall table.

We do not offer a single path and ask students to fit it. Whether a student is taking on the International Baccalaureate® Programme, building the learning strategies and self-advocacy that define the Roxbury Center for Learning & Leadership, or pursuing a serious body of work in our Art Major program, the point is the same: a personalized pathway with the right balance of challenge and support, designed with that student and owned by that student. Expert teachers guide the pathway. Students do the driving. That combination — real rigor and real individualization, together — is rarer than it should be.

Beyond the classroom, our students are athletes, musicians, artists, and leaders. They compete, perform, create, and serve. These are not extras added on top of the academic program; they are where character gets practiced. Our core values name what we expect of one another here — Belonging, Engagement, Collaboration, and Growth. We welcome and value people for who they are. We show up and take part. We are honest, reliable, and accountable to each other. And we assume that every one of us, students and adults alike, still has learning to do.
 
What moves me most is watching students stretch past what they believed they were capable of. That happens because of the adults here. Our faculty and staff do not simply teach — they mentor, coach, push, and stay.
 
They understand that an education is preparation for a complicated world, and that the measure of our work is not what our students know at graduation but what they do with it afterward.
 
There is no better way to understand Cheshire Academy than to see it. Visit campus, walk the grounds, meet our community, and judge for yourself how a school more than two centuries old keeps preparing students for a world that will not sit still. We take real pride in seeing the full potential in every student — and in helping them imagine a future they had not yet pictured for themselves.
 
I look forward to welcoming you.
 

My best,

Tom Woelper P’26

Head of School

VIRTUAL OPEN HOUSE

June 16, 2026, 6-8 p.m.

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