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Strategic Plan 2023-2028


The story of Canterbury School is one of a values-driven, student-centered community whose springboard into its second century has been marked by extraordinary momentum. Our academic program prioritizes intellectual rigor and innovative mindsets and has led generations of students to their greatest individual outcomes. Moreover, the differentiating role of our Catholic heritage as the foundation of a service-minded interfaith community continues to fortify a commitment to moral leadership and fuel a mission that remains relevant and resonant.

Yet, even as we are bolstered by this momentum and affirm the foundational commitments that continue to define and drive our program, we acknowledge continued challenges. How do we retain the core values that brought us with strength to this time while also ensuring our ability to thrive in the 21st century? How do we go beyond preparing students for college and ready them for a world that will push them in ways we cannot yet imagine? How do we go beyond teaching young people the importance of values and empower them to live and lead with those values for the betterment of others? This is the calling before Canterbury School. 

The strategic plan that follows not only declares a path to fulfill that calling but reflects our bold assertion that Canterbury is the best small boarding school, a leader and model for how students can—and should—be mentored intellectually, spiritually, socially, emotionally, and physically in their journey from adolescence to adulthood. Our plan is exciting and aspirational, worthy of our past, vital for our future. And to be sure, its success relies on what we all share: an unrelenting commitment to providing the transformative high school experience that current and future Canterbury students need and deserve.

Excerpts from Head of School Rachel Stone's presentation of the Canterbury School Strategic Plan 2023-2028 to an audience of alumni, parents, school leaders, education consultants, and trustees (January 2023).  

With great intention, our plan is anchored in all that we hold paramount—People, Purpose, Program, and Permanence—and draws out a set of strategic imperatives central to realizing our vision for Canterbury’s future. These imperatives serve as enduring points of focus as we anticipate the demands of tomorrow while delivering the most comprehensive educational experiences that our students need to live, learn, and lead with purpose today. Finally, the plan conceptualizes myriad opportunities from which our lofty strategic imperatives can produce real, tangible results. 

Click the photos below to learn more about the strategic imperatives and opportunities within the four core principles that serve as the framework of our plan.



Firmly rooted in our conviction that we are the best small boarding school, this plan seeks to elevate and strengthen the transformational nature of the Canterbury experience. It trusts our unique ability to provide students with opportunities for powerful learning and personal growth. It is confident in the enduring importance of our institution and the higher purpose that it serves. Finally, it is a plan that assumes a constant process of re-examination and re-invigoration. It will leave Canterbury nimble, revitalized, and well-resourced in 2028.

And so we go forth with a commitment to these new ideas and opportunities and with a determined resolve to implement them. Indeed, we go forth empowered by People, Purpose, Program, and Permanence, excited for Canterbury to emerge as an even stronger and truer version of itself.


If you have questions or would like to further discuss our exciting plans for the future of Canterbury School, please contact:

Rick Henderson P '25
Chief Advancement Officer