Trinity-Pawling School

Trinity-Pawling School is an all-boys Episcopal boarding and day school in Pawling, New York, about 70 miles north of New York City. It serves middle school, high school, and post-graduate students, with enrollment between 200 and 300. That scale is deliberate — small enough that faculty know every student by name, large enough to run a full academic program across multiple grade levels.

Teaching at Trinity-Pawling carries three core expectations: classroom instruction, athletic coaching, and a role in residential life. Faculty live inside the community they help run. That structure gives teachers real influence over school culture, not just subject outcomes. For candidates drawn to single-gender education, the daily visibility is a meaningful part of the job.

Because the student body is all male, faculty often help young men build habits of accountability and peer leadership alongside academic skills. That focus runs through advising, dorm life, and athletics — not just the classroom. It makes Trinity-Pawling a different teaching environment than a co-ed day school.

The school holds roughly $90 million in net assets and generates close to $26 million in annual revenue. Those figures support competitive faculty salaries and stable institutional finances. Residential positions typically include on-campus housing and meals — benefits worth thousands of dollars monthly that a base salary number alone can hide. Language faculty will find active programs in Mandarin, French, and Spanish, with additional openings in humanities, sciences, and student-life roles.

Faculty searches for teaching jobs peak in late winter and spring before each academic year. Administrative and leadership searches run on longer timelines. For teachers seeking a boarding school career in New York's Hudson Valley with a clear single-gender mission, Trinity-Pawling is worth a serious look.