Why Trinity-Pawling?

It's where boys find their greatness.

We guide our students to become young men of integrity who can rise to the challenges of an ever-changing world. Our distinctive programs encourage boys to achieve greatness within themselves and their community.

The Practicum for Civic Leadership offers multiple active learning opportunities for students to gain hands-on, 21st century skills. Our Effort System provides a guide for making good decisions, and it builds a foundation for continued self-improvement and self-reflection. And our Center for Learning Achievement gives students the support they need to thrive in our vigorous academic setting. 

I needed a school that would give my son the opportunity to prove himself and T-P does just that. As a parent, it feels so great to see my son excited about being at school.Cynthia Bolding P’20

Virtual Trinity-pawling Experience

A series of 4 interactive webinars with key members of our school community

At Trinity-Pawling, we believe learning takes place in a community. While nothing can be a substitute for experiencing Trinity-Pawling in person, we are excited to offer you this series of virtual webinars to stay connected, answer your questions, and introduce you to the School community. Headmaster Bill Taylor, our Pride Parents, alumni, and students truly enjoyed sharing their experiences and we hope you enjoy watching the webinars and learning more about the value of a Trinity-Pawling education!

Headmaster Bill Taylor answers parent questions during an interactive webinar

Q&A with Headmaster Taylor

Join Headmaster Bill Taylor and Director of Admissions JP Burlington ’95 for a Q&A session about the Trinity-Pawling experience – including our distinctive programs, outstanding faculty, the brotherhood, and a community like no other!


Trinity-Pawling young alumni speak about their experiences at the School in an interactive webinar

Q&A with Alumni

Join a group of recent Trinity-Pawling graduates to learn about the valuable education they received and how it prepared them for college and beyond.

Current and past Trinity-Pawling parents answer questions and speak about their experiences in an interactive webinar

Meet our Pride Parents

Hear from a fantastic group of current and past parents about their experiences at Trinity-Pawling — from preparing your sons for the boarding experience to the many ways Trinity-Pawling helps boys grow into men.


The 2019-2020 Prefects speak about their Trinity-Pawling experiences in an interactive webinar

Meet the Prefects

Meet our current student leaders to learn all about life on campus. They each have a special focus – school spirit, the arts, service, academics, honor, and victuals (that's food!) – they're eager to share what a day in the life at T-P is all about.

WE call ourselves the pride.

We’re proud of each other and the goals we’re all working toward, independently and together. We are a school of 300 boys from all across the nation and the world. Trinity-Pawling is a community that values and inspires leaders, friends, athletes, global citizens, and men of character. Explore below to learn more!


Why All-Boys?

Portrait of a Graduate

Explore Our Viewbook