Canterbury School

Teaching and Staff Jobs at Canterbury School

Canterbury School is a Catholic, college-preparatory boarding and day school for grades 9–12 in New Milford, Connecticut. Founded in 1915, the school enrolls between 301 and 500 students on a hilltop campus in Litchfield County, roughly 1.5 hours northwest of New York City. New Milford itself offers tree-lined streets, local galleries, and a walkable downtown just three minutes downhill from campus—a rare setup that gives faculty rural quietness without urban isolation.

The school's Catholic identity shapes teaching culture through collaborative leadership rooted in moral and ethical values. At Canterbury School, faculty model commitment to growth and engage students beyond classroom walls, grounding leadership in service rather than hierarchy. This philosophy extends to hiring: the school seeks educators willing to live that framework day-to-day alongside students.

Canterbury operates as both boarding and day institution, creating flexibility in faculty roles. Some teachers serve as dorm parents and advisors; others remain primarily day-based. This mix allows positions to fit different life stages while deepening residential faculty connection to student life during evenings and weekends. The curriculum includes traditional college-prep disciplines alongside language programs in French, Latin, and Spanish.

Strong financial footing supports competitive compensation and ongoing campus investment. Canterbury School's substantial net assets and consistent revenue signal institutional stability—important context for educators planning long-term careers. Recent leadership searches, including a Dean of Faculty position, reflect the school's commitment to building its educational vision.

*View current openings at Canterbury School.*