101 Aspetuck Avenue
|Type||Private, Day & Boarding School|
|Motto||"Supercertari semel traditae sanctis fidei"|
(To fight valiantly for the faith once delivered to the saints)
|Religious affiliation(s)||Roman Catholic|
|Founders||Nelson Hume and Henry Havemeyer|
|Head of School||Rachel E. Stone|
|Chaplain||Rev. Timothy S. Valentine|
30% day (2019-20 school year)
|Average class size||12|
|Student to teacher ratio||6:1|
|Campus size||150 acres (2 km²)|
|Color(s)||Navy and Columbia Blue|
|Sports||18 sports, 46 JV/Varsity Teams|
|Accreditation||New England Association of Schools and Colleges|
|Publication||Carillon (literary magazine)|
|Endowment||$33 Million |
|Tuition||Day - $46,600|
Boarding - $62,300 as of 2019-20
|Director of College Counseling||Sarah Ferland|
|Dean of Faculty||Wright Danenbarger|
|Assistant Head of School for Student Life||Peter LaVigne|
|Dean of Academics||Sue Roberts|
|Director of Admissions||Matt Mulhern|
|Athletic Director||Jim Stone|
Canterbury was founded in 1915 on the aspiration of two men: Henry O. Havemeyer, scion of a wealthy family which made its fortune in sugar refining, and Nelson Hume, a Catholic schoolmaster. They intended to establish a Roman Catholic school where young men could be guided in their religion and be prepared to attend Ivy League universities.
The school was established in New Milford, Connecticut, on the location of the former Ingleside School for Girls. Hume became the first headmaster of the school. From its start with 16 enrolled students, Nelson Hume guided the school through two world wars and the great depression until his death in 1948. He was succeeded as headmaster by Walter Sheehan, John Reydel in 1973, Roderick Clarke in 1978, Thomas Sheehy in 1990, and Rachel E. Stone in 2016. Canterbury became co-educational in the fall of 1971. The School now enrolls around 320 boarding and day students on its campus in New Milford. Canterbury School celebrated its centennial in 2015.
Old School House contains the language and history departments; the majority of language and history classes are held here. Canterbury offers Spanish, French, and Latin. 
Hume Hall contains the theology and mathematics departments on the upper level, and the science department on the lower level. The Hume building also houses Canterbury's newly renovated Maguire Auditorium on the upper level.
Steele Hall was completely renovated in 2009. It contains the Copley Library, Admission and administrative offices on the upper level, and the student lounge, snack bar, mailroom, faculty room, dining hall, and lecture room on the lower level.
Duffy House contains art space and studios renovated from the old dining hall.
The Old Gym's first floor space has been renovated for the Stephen '43 and Lacey Hume Music Center, the L. Michael Sheehy '56 Choral Classroom, and rehearsal spaces.
Canterbury School has eight residence halls that provide housing for about 250 students. Each residence hall contains faculty apartments that range from the size of town houses to smaller one-bedroom suites. Canterbury also has built single family homes on campus, providing housing for some faculty, such as the Headmaster's House, located on the corner of Aspetuck Avenue and Elkington Farm Road.
Sheehan House (née Middle House) is named for Canterbury's second headmaster, and is located in center of the lower campus. Simply referred to as "Sheehan" by students, it houses upper form boys. On Graduation, graduating VI formers walk from Sheehan to the Chapel, a tradition since 1976.
Carter House (née South House) is located on the lower campus and houses upper and lower form girls.
Duffy House (née North House) is located on the northern end of the lower campus and houses lower form girls. It contains a faculty townhouse on the western end of the building, in space that was converted from administrative offices. The school's art department is also located on the ground floor.
Hickory Hearth is located at the southern end of the lower campus and provides space for six students (boys) and three faculty members.
Havemeyer House is located on the upper campus and houses upper form boys. Nicknamed "Havey" by students, it contains two faculty townhouses which bookend the dorm.
Carmody House is located on the upper campus and houses lower form boys. Identical to Havemeyer, two faculty townhouses bookend the dorm. It is named after the Carmody family, one of the founding families of the school.
South House is a newly constructed building on the lower campus between Hickory Hearth and Carter House that houses upper form girls.
Chapel of Our Lady was built in 1928 and expanded in 1959. It can seat 300. Mass is celebrated every Sunday during the school year in the Chapel at 11:30 AM. The bottom floor of the chapel contains a classroom. Its stained glass windows have been recently restored. The chapel's carillon is named for alumnus Mel Ferrer '34.
Chaplain's Residence is the oldest building on campus and has had various uses, including acting as Canterbury's first chapel.
The Athletic Center commonly referred to by students as the "NAF" (New Athletic Facility), contains the Canterbury Ice Hockey Arena (1975), the Castellini/Saxe Squash Pavilion (five courts), the field house (with three basketball courts), weight room, trainers room, and a wrestling room.
Pigott Basketball Arena was added on to the Old Gym complex in the 1960s and includes the varsity basketball arena and locker room facilities.
William R. Higgins '53 Aquatic Center, opened in the fall of 2008, provides a new 8-lane, 25-yard pool and diving facility. It is located in the same building complex as the Pigott Basketball Arena.
Outdoor facilities include 8 tennis courts, a multipurpose turf field, other multipurpose grass playing fields, and baseball and softball diamonds with dugouts 
Canterbury Offers 19 Varsity Teams in Baseball, Basketball, Field Hockey, Football, Hockey, Lacrosse, Squash, Soccer, Softball, Swimming, Tennis, Volleyball, and Wrestling. All students participate in sports and Canterbury fields Junior Varsity, Thirds and Fourth teams in support of its varsity supports.
The school competes in the New England Prep School Athletic Conference (NEPSAC).