Welcome to a Life-Changing Opportunity…


What is “best” is different for every child, and in its 226-year history, Cheshire Academy has been known for its program of individualized attention for each student. Parents commend us for meeting students where they are in their academic and social development, and for serving the needs and aspirations of a range of learners. We do this exceptionally well.

Most students enter the Academy in their freshman or sophomore year; however, joining the school as a junior, senior or postgraduate is also common, and for some, an opportunity to repeat a year. What all applicants share in common is a desire for top academics in a supportive and attentive high school environment

Take your next step in the quest for what’s next: schedule a virtual tour of campus, plan an online interview, or have your initial questions answered via phone or email – my staff and I would love to talk with you.  You will find at Cheshire Academy the options you seek to support and advance your child’s interests, talents, and academic career.


Sara Lynn Leavenworth
Director of Admission


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NEW: Updates and resources related to COVID-19 can be found HERE.