SSL Certificate


We believe a man of great character
exists in every boy,
and if he finds that man within himself,
the trajectory of his life
will shape our world for the better.


In the classroom, we continue to transform student performances with a strong core curriculum and rigorous expectations.

The Effort System continues to open students' eyes to their full potential. Faculty remain key to our entire endeavor.

Brotherhood and pride have never been stronger in the student body than they are today.

Our students are enjoying great college success.

We offer 13 varsity sports and remain proudly competitive in the prestigious Founder's League.

We've invested in all our facilities, and the campus now better reflects the quality of our programs. We believe more strongly than ever in the power of all-boys education.


  • We will fortify and expand the reputation of Trinity-Pawling so that more boys and their families know that T-P is the best place—bar none—to galvanize a young man's highest potential.
  • We will launch a movement of alumni, parents, friends who are strongly engaged with the School and with each other. 
  • We will raise between $35 and $45 million for the endowment and capital projects. 
  • We will honor and invest in faculty.

Once in the history of a school, a moment like this arrives. We have sizable momentum on which to build. Now Trinity-Pawling is ready to surge forward and claim a stronger place in the realm of education. The task before us is both simple and dramatically ambitious: we must secure the financial footing of our School as never before.

To learn how to partner with the School, please contact Director of Advancement Regan LaFontaine at 845-855-4838.

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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