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Head of School Reflections



The Case for Small Boarding Schools. The Case for Canterbury School.

If you are considering independent high school for your child, I cannot encourage you strongly enough to take a close look at small boarding schools.*


Of course, you seek an excellent, rigorous academic program integrally tied to a competitive college placement process. You want opportunities for both novice athletes and those vying for spots on college rosters. You look for programs that offer theater, studio art, and music; community service; myriad clubs and travel experiences; and leadership development.

And certainly, you want your child to be surrounded by a team of adults who value your role as parent/guardian and who will commit to knowing, nurturing, challenging, affirming, and standing by your child. Faculty who appreciate that the path through adolescence is rarely straight. A community that knows from experience and wisdom that teenagers are an even mixture of child and adult and that the ingredients of one’s high school journey should include both laughter and tears, mistakes and victories, new experiences, and plenty of growth along the way. 

Although it sounds too good to be true, this is exactly what small boarding schools offer…for all of our students and not just those at the margins. Moreover, these expectations and programs are only the start.

I believe that the most remarkable and differentiating aspect of small boarding schools is that they value the equal importance of academic success, personal growth, and community engagement when it comes to learning, living, and leading:  

  • Our students are expected to play a meaningful, responsible role within our community broadly; among classmates, teammates, and dormmates specifically; and throughout all of the spaces in between. Your child’s actions and opinions play an impactful role in building the culture of community.
  • This critical degree of expectation and responsibility fosters a level of accountability paired with independence and leadership development that only exists in small boarding schools. Your child has unlimited opportunities to develop as a leader.
  • Students take ownership of their individual and community experience, from their academic journey and athletic interests to new clubs, weekend activities, service work, and travel. Your child takes charge of their high school experience.

To put it simply, as a student at a small boarding school, your child will be in a position to navigate the complexities, uncertainties, and opportunities of high school within an infrastructure designed for teenagers to find their footing and voice as they explore their ambitions. An infrastructure built from expertise in healthy adolescent development and galvanized by faculty committed to walking this journey alongside you and your child…a journey that leads far beyond excellent college preparation and placement to a life of passion and purpose.

Furthermore, I believe that Canterbury is the best small boarding school.

For students seeking the foundations for success in life, Canterbury School offers a small boarding school experience that provides an extraordinary combination of opportunities for students’ academic success and personal growth. 

  • We philosophically believe that high school is too important to rush through by checking a series of boxes. Students deserve a personal, transformative experience where they can be themselves as they become their best selves.
  • We take our academics seriously, are proud of our college outcomes, and celebrate each other’s successes along the way.
  • Our students understand and model that academic excellence should be collaborative, not competitive; that asking for help is a sign of strength and independence; and that faculty can have high expectations of them—and root for them—at the same time. 
  • We partner academic tradition with innovation; our students learn to write with clarity, speak effectively, think critically, and be digitally literate.
  • We remain committed to the “triple threat” approach to faculty hiring by recruiting, supporting, and sustaining student-centered faculty whose passion for teaching, coaching, and advising is matched by their focus on being in their students’ corners. Teachers at Canterbury meet students where they are and work tirelessly to help them see, believe, and reach their potential.
  • We champion the idea that high school athletes should have the opportunity to experience new sports and develop as student-athletes and leaders through a range of athletic endeavors. 
  • We lead with values. Our Catholic heritage sparks conversations about service and spirituality, inspires the development of ethical leadership, and ensures an inclusive, interfaith community founded on values and justice.
  • We understand that each student arrives on our campus with a unique set of experiences, needs, and aspirations. 

As the best small boarding school, Canterbury invites you to participate in the most comprehensive version of a high school experience as students, athletes, artists, community members, and servant leaders. As a Saint, you will grow, contribute, and lead in transformational ways. You will learn that Saints show up for Saints. And you will call our hilltop your home.

Rachel Stone P ‘23, ‘24

*By my definition, those with fewer than 350 students.