SSL Certificate

Thank You!

Nearly 300 alumni, parents, and friends turned up to make this Reunion and Homecoming Weekend one to remember.

Whether you came from near or far, we’re glad you made it! Mark your calendar for October 4-5, 2019 when we’ll do it all again!


Save The Date

Reunion Weekend 2019

October 4 & 5, 2019

Congratulations to the Trinity-Pawling Athletic Hall of Fame Class of 2018!

The Athletic Hall of Fame was established in 1998 to honor former teams, student-athletes, and coaches who have reflected honor upon Trinity-Pawling by virtue of outstanding performance and exemplary contributions to their alma mater, community, and profession, and in doing so, reflect the philosophy of a college preparatory education and the ideals of sportsmanship. The 2018 Inductees are William A. Cooper P'75, '79, C. Stephen Harrington '68, and the 1976-77 Soccer Team. 

The Induction ceremony took place Saturday September 29th during Homecoming & Reunion Weekend.

Hall of Fame Members > 

Classes celebrating milestone reunions

Honor Guard              1964

1969                             1974

1979                             1984

1989                             1994 

1999                             2004

2009                             2014          

Please update your contact information to receive the latest updates from your class!


View the full list of Trinity-Pawling room blocks and other lodging information for Reunion Weekend.

Questions? Reach out!

Janet Hubbard P'07, Director of Advancement Operations

Give to the Trinity-Pawling Fund

Make your reunion gift today!
We hope you will consider a special gift 
to the Trinity-Pawling Fund in honor of your reunion! 

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.

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.

As a convenience, Trinity-Pawling School links to Google Translation which provides an automated translation of our website. The tool is not perfect, and the context of the copy may not be precise when it is translated. As a result, sometimes the translation may lose some of its intended meaning. Therefore, Trinity-Pawling School cannot guarantee the accuracy of the converted text. Where there is any question, the English version is always the authoritative version of the website.

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