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Express Yourself.

You might shine in a leading role or delight the crowd as the comedic sidekick. However you're cast, you'll have three opportunities to act in a main-stage play or musical each year produced by the Drama Society. If you're itching to write your own play, direct a short skit, or keep us guessing with improv performances, there's room for you, too. Not made for the spotlight? The show can't go on without your help backstage on lighting and set construction!

Friday Evenings in Gardiner Theater
Open to all students, faculty, and staff!
9:00 to 10:00 pm

The IMPROV SPACE introduces participants to the world of improvisation: developing the core principles of listening, accepting and celebrating mistakes, working as an ensemble, and trusting your own ideas. Better yet - it's fun! Trinity-Pawling's IMPROV SPACE is a great way to break out of your comfort zone, build confidence, and learn to express creative ideas clearly and joyfully. Join us!

Past Productions

Questions? Reach out!


Kent Burnham
Director of Theater Arts

Let NYC inspire you.

The hub of art and culture - New York City - is our neighbor to the south! Throughout the year, you'll hop on a train to visit some of the world's finest museums, galleries, and concert halls. Join our Broadway/Off-Broadway Theater Series program to see highly-acclaimed Broadway and off-Broadway productions.

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.

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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