Trinity-Pawling School held its 107th Commencement Exercises on Sunday, May 25, 2014, and celebrated the graduation of 89 students.
Trinity-Pawling's Stepping Up ceremony was held in All Saints' Chapel on Saturday afternoon, May 24th. Stepping Up is the School's in-house Commencement as we bid farewell to the seniors and usher the underclassmen up to the next grade level. It is a poignant ceremony, steeped in a century of tradition.
Eleven Trinity-Pawling Football players have committed to play at the collegiate level, a record high for our program, which has a rich tradition of collegiate participation.
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  • September, 2014
    • WedSep03 Early Sports - By Invitation Only, arrive before 12:00 PM
    • ThuSep04 New International Students arrive by 12:00 PM
    • ThuSep04 All Seniors and Post-Graduates (not Early Sports) return by 2:00 PM
In the spotlight

A Commitment to Character

As we prepare young men for the world beyond Trinity-Pawling, we seek to convey this fundamental lesson: Character is the single most influential force to propel us forward - whether academically, physically, socially, or spiritually.

Trinity-Pawling has so much to offer!

Check out everything you can do and be in the pages on our site.  And if you'd like to contact us, we'd be happy to hear from you.  You can reach the admission office at 845-855-4825 or by email at

Not Just In the Classroom

What makes Trinity-Pawling unique? The Effort System is at the heart of everything we do.

The Pride

At Trinity-Pawling, every boy is a three-season athlete.  Whether he is learning the basics or has been excelling for years, he is part of the School's century-old athletic tradition.  T-P competes in the Founders' League, a highly competitive arena showcasing some of the nation's best prep school talent. T-P offers 13 interscholastic sports with 30 teams.

We're Seriously Creative

The Arts are an integral part of every Trinity-Pawling student's education. Whether they wish to develop existing talents or experiment with an entirely new form of expression, each student will have at least one year of music, theater, visual art or art history.


As a parent or guardian of a Trinity-Pawling student, you are a welcome member of the community. Your involvement through event attendance, participation in the Parents' Association, or simply staying connected is appreciated.

This could be you!

Over 100 years ago, Frederick Luther Gamage, Trinity-Pawling's Founding Headmaster, said, "Whether a boy succeeds or fails in the first instance at everything he tries is irrelevant.  The only boy who truly fails is the boy who fails to try."  Today, a century later, 315 boys live learn and grow together in an environment that fosters commitment, effort and character across the board.

Stay Connected!

Trinity-Pawling has a rich tradition of alumni connectivity. We want you to participate in the life and vitality of the School. Through this engagement, alumni will help Trinity-Pawling propel forward.

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