The Winchendon School

The Winchendon School operates a dual-campus model: a boarding school in Winchendon, Massachusetts, and a day school in New York City. Together, the two locations serve roughly 400 students in grades 9 through post-graduate year. This structure is unusual among independent schools and creates flexibility for candidates who may prefer either residential or day-school teaching environments.

The Winchendon School emphasizes language instruction across its curriculum. The school offers American Sign Language, French, and Spanish alongside English as an Alternative Language — a substantial commitment that shapes both course selection and campus culture. For language educators, this breadth signals serious institutional investment in multilingual literacy.

Faculty roles span traditional subject areas and specialized language instruction. The school hires teachers for high school and post-graduate cohorts, coaches for athletic programs, and administrative staff to support both campuses. Because Winchendon operates boarding and day tracks, roles vary: residential faculty at the Massachusetts campus may live on-campus, while NYC-based educators typically commute. Both contexts demand engagement with students beyond the classroom.

The post-graduate year itself distinguishes The Winchendon School. Post-grad students often require different curricular pacing, mentorship intensity, and life skills support than traditional high school students. Teachers and advisors working with this cohort take on advising roles that extend into college planning and transition preparation.

For educators interested in language-rich, multilingual environments or those drawn to post-graduate instruction, The Winchendon School offers a less common pathway. The dual-location structure also appeals to candidates with geographic flexibility or interest in comparing boarding versus day school cultures.