History & Catholic Heritage

Nurturing Young Minds for More Than a Century

From the initial group of 18 students who began their journey in 1915 to the vibrant community of 325 students today—and more than 5,000 alumni who have ventured to renowned colleges and universities both here and abroad—the students who thrive at Canterbury are those who embody the School's founding values of intellectual achievement and moral character.

Our Founding

Our Founding

In the fall of 1914, schoolmaster Dr. Nelson Hume and entrepreneur Henry Havemeyer began working together on a bold dream—to start a school operated by Catholic laymen who, independent of a religious order, would prepare boys for the best colleges and universities in the country while nurturing them in their faith.

In seeking a location for the new boarding school, Dr. Hume wanted proximity to New York City, yet desired the allure of a rural backdrop. He discovered this in New Milford, Connecticut, atop a hill near Elkington Farm. With its three main buildings and vast playing field, shaded pathways, and striking elms, Dr. Hume instantly recognized it as the ideal spot.

Dr. Hume would serve as Canterbury’s founding Headmaster until 1948 and as its initial Director of Admission. The first boy to officially enroll at Canterbury was Cyril Clemens, Mark Twain’s distant cousin, followed by Henry Havemeyer’s son, Henry. They and an additional 16 students in the School’s charter class started in the fall of 1915.

Male and Female students in old car from '60s

Evolution & Growth

Evolution & Growth

Nelson Hume guided the school until his death in 1948, when Walter Sheehan succeeded him. He was followed by John Reydel in 1973, Roderick Clarke ’46 in 1978, Thomas Sheehy in 1990, and our current Head of School, Rachel Stone P ’23, ’24, in 2016.

In the fall of 1971, Canterbury embarked on a new initiative that would enrich the School community forever: it admitted nine female students, each of whom paved the way for future female Saints and inspired all students with their courage and tenacity.

Through the years, the campus’s physical plant expanded substantially from its original three buildings—including the Chapel of Our Lady, Nelson Hume Hall, Maguire Auditorium, Robert M. Steele ’72 Hall, David C. Copley ‘70 Library, Alumni Memorial Gym, Athletic Center and Field House, several new dorms, and many more impressive facilities.

In 2002, Bob Steers ’71, P ’11 joined the Board of Trustees and assumed the role of President five years later. He would go on to become the second longest-serving Board president—behind only Henry Havemeyer—before stepping down in 2023. Those years marked an era of remarkable success and momentum for the School.

An Era of Unprecedented Momentum

An Era of Unprecedented Momentum

The School entered its second century in 2015, ushering in a period of remarkable momentum.

In these recent years:

Two transformative facilities have elevated the student experience: the Steers Center, a sprawling 22,000-square-foot hub for innovation and student life, and Hamilton Stadium, featuring a cutting-edge turf field, track, bleacher seating, and stadium lighting.
Distinctive programs such as the Donovan Center for Learning; D’Amour Center for Faith, Service & Justice; and the Coleman Family Digital Media Lab differentiate our School and shape the ways students grow as intellectual and ethical leaders.
The sheer number of academic, athletic, artistic, and co-curricular offerings rivals those found at our larger peer schools.
Exemplary college placements span the Ivy League and other top-tier institutions, and a consistent third of each graduating class goes on to compete in college athletics.
Our endowment has seen a threefold increase, and the most successful Annual Fund in School history was achieved.
Our 2023 Strategic Plan—People, Purpose, Program, Permanence—charts a bright and ambitious course for our future.

Our Catholic Heritage Today

Our Catholic Heritage Today

What does our Catholic heritage look like today? How, when, and why do our students experience faith while at Canterbury?

Canterbury is an inclusive interfaith community grounded and informed by Catholic values. Our families come from a wide range of religious backgrounds—a testament to the welcoming nature of our campus and the importance we place on an education that fosters moral development and spiritual discovery.

We see and support three pathways of faith for our students:

An Opportunity to Grow in Faith

Some students arrive with a strong faith foundation and wish to continue deepening that commitment and growing in that faith while here. Catholic students may participate in Canterbury’s Confirmation program, aspire to be a Sacristan, and attend Mass. Students who bring other faith backgrounds may attend a local place of worship, join the Interfaith Council, or help lead initiatives on campus via the D'Amour Center for Faith, Service & Justice.

An Introduction to Faith

Some students arrive with little exposure to or experience with faith and are introduced to prayer, religious traditions, and a foundation of faith while at Canterbury. The seeds of faith are planted, and these students have opportunities to learn more and decide how they want to carry faith forward in their lives.

A Framework of Respect for Faith Traditions

Some students arrive without a connection to faith and ultimately decide that religion will not play a formal role in their lives. Still, while at Canterbury, they do learn to respect different religious traditions and understand why faith plays an integral role in the lives of others.

Heads of School

Headmaster Nelson Hume P ’41, ’43, ’45
1915–1948

Headmaster Walter Sheehan P ’62, ’73
1948–1973

Headmaster John Reydel
1973–1978

Headmaster Roderick Clarke ’46
1978–1990

Headmaster Thomas P. Sheehy III P ’92, ’98, ’04
1990–2016

Head of School Rachel E. Stone P ’23, ’24
2016–present

Canterbury has remained deeply anchored in the same academic vision, progressive spirit, and values-centered approach that guided its founding more than 100 years ago. These principles continue to differentiate us in today's boarding school market and underscore our unique ability to develop tomorrow's intellectual and ethical leaders.

The Canterbury Medal

Service • Dedication • Loyalty

Instituted in 1994, the Canterbury Medal honors an individual or group who has demonstrated unparalleled devotion to Canterbury School. By awarding the medal, the School honors the individual or group for extraordinary efforts in advancing the mission of the School.

Nurturing Young Minds for More Than a Century

Heads of School

Headmaster Nelson Hume P ’41, ’43, ’45 1915–1948

Headmaster Walter Sheehan P ’62, ’73 1948–1973

Headmaster John Reydel 1973–1978

Headmaster Roderick Clarke ’46 1978–1990

Headmaster Thomas P. Sheehy III P ’92, ’98, ’04 1990–2016

Head of School Rachel E. Stone P ’23, ’24 2016–present