Cheshire Academy

Founded in 1794, Cheshire Academy is one of Connecticut's oldest independent schools, enrolling 300 to 500 students in grades 9 through 12 plus a postgraduate year. The campus is in Cheshire, CT, about 20 miles north of New Haven, and serves both boarding and day students in a secular community.

Faculty work across a wide range of learner profiles. The Roxbury Academic Support Program provides structured academic guidance for students who need it. The International Baccalaureate Diploma Programme serves those pursuing a globally recognized credential. A teacher may work with both populations in the same term, which keeps the work varied and the expectations broad. Language instruction spans Chinese (Mandarin), French, and Spanish.

The arts have real structure here. An Art Major course builds a direct pathway for students applying to college-level studio programs. Athletics run from championship competitive teams to recreational programs for developing athletes, and afternoon activities include theater and music. Faculty routinely hold responsibilities outside their primary subject — that dual role is standard, not occasional.

Residential faculty join student life well beyond the classroom. Connecticut independent schools in this enrollment range typically offer salary, health benefits, and on-campus housing for boarding staff. In a high cost-of-living state, that housing can represent significant compensation that a base salary figure alone won't show. The school reports net assets near $38 million, a useful data point for candidates evaluating long-term stability.

Open teaching and staff positions at Cheshire Academy span academic departments, student life, athletics, and administration. Because the school is small, each hire shapes curriculum and culture in ways that rarely happen at larger institutions.