About

Cluett in the snow

Founded in 1907, Trinity-Pawling School is an all-boys college preparatory school located in Pawling, New York. We serve 300 boys in grades 7-12 and offer a postgraduate program. Our beautiful 230-acre campus is situated just 60 miles north of New York City. The dynamic learning environment at Trinity-Pawling emphasizes innovation, creativity, critical thinking, and a commitment to experiential learning. With 90% of faculty living on campus, our students learn and grow in a close-knit and caring community. They are guided by dedicated teachers who are also their coaches and dorm parents, establishing strong faculty-student collaboration that provides 24/7 learning. 

We offer over 100 academic courses and 20 AP courses, competition in 13 New England Founders League sports, and a diverse menu of clubs and activities, allowing students to explore and discover their interests and passions. Most importantly, our graduates leave with confidence, integrity, and lifelong friendships. The experience at Trinity-Pawling combines a timeless commitment to character with a dedication to prepare young men for an ever-changing world.

Mission & History

Meet the Headmaster

Campus & Facilities

Everything the School did for me — the people I met, the doors it opened for me — has changed my life. I am forever indebted to Trinity-Pawling for the friendships and memories it provided me.
Bryan Cahill ’15