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DISCOVER WHAT CHESHIRE ACADEMY HAS TO OFFER! LEARN MORE

Cheshire Academy written in white lettering with a solid dark blue background.

MEET OUR HEAD OF SCHOOL

Tom Woelper

Tom Woelper

A Message from the Head of School

What drew me to Cheshire Academy, and I believe will also draw you here, is our remarkable ability to transform lives through a truly personalized approach to education. Since 1794, we have understood that every student’s path to success looks different – and that’s precisely what makes our community so extraordinary. 

When you step onto our historic 104-acre campus, you’ll find yourself immersed in a vibrant global community where students from 27 countries and 15 states come together to discover their passions and potential. But what truly sets us apart isn’t just our diversity – it’s how we embrace and nurture each student’s individual journey. 

At Cheshire Academy, we don’t believe in a one-size-fits-all approach. Whether a student is challenging themselves through our rigorous International Baccalaureate® Programme, finding support through our innovative Roxbury Academic Support Program, or pursuing their artistic passions in our Art Major program, we create unique pathways that allow every student to thrive. This combination of individualized support and academic excellence is rare in today’s educational landscape. 

Beyond the classroom, our students are musicians, athletes, artists, and leaders. They compete on our 27 athletic teams, perform in our theater productions, create in our art studios, and engage in meaningful community service. These experiences aren’t just extracurricular activities – they’re integral to developing character through our Eight Pillars of Bowden: respect, responsibility, caring, citizenship, civility, morality, fairness, and trustworthiness. 

What excites me most about leading Cheshire Academy is witnessing how our students stretch beyond their comfort zones, embrace new challenges, and discover capabilities they never knew they had. Our faculty and staff don’t just teach – they mentor, guide, and inspire. They understand that education is about more than just academics; it’s about preparing students to be thoughtful, engaged citizens of an increasingly complex world. 

There’s no better way to understand the Cheshire Academy difference than by experiencing it yourself. Visit our campus to walk our grounds, meet our community, and witness how we honor our 230-year legacy while preparing students for a rapidly evolving world. We pride ourselves on seeing the full potential in every student and helping them envision futures they never thought possible. 

I look forward to welcoming you to our community. 

Sincerely,

Tom Woelper
Head of School

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