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You're on the verge of something big.
Jump in to find out.

Our Middle School curriculum is built on five themes that will help boys gain a deeper understanding of their self-awareness, creativity, character and honor, and their place in an ever-changing world. 

With just 30 students in our Middle School, our small classes allow teachers to get to know the real boys. And they will guide them on a journey of self-discovery to uncover their gifts and talents, and lay the foundation for future success.

8th Grade Boarding at Trinity-Pawling
Get ready. Go far.

We’re going to let you in on a secret: boys don’t have to wait until Upper School to become a boarding student at Trinity-Pawling. A selection of 8th grade boys will now be welcomed each year to join our boarding community.

With limited enrollment, our 8th grade boarding program is developmentally appropriate, individualized, and intentionally designed to nurture Middle School boys in preparation for the Upper School. Students in the 8th grade will be engaged in a dynamic and comprehensive boarding school experience. Young scholars will immerse themselves in the boarding program and take part in a selection of vigorous activities which allow boys to experiment and explore: arts & innovation, science & math, English language mastery, and cultural field trips. Boys will also be able to benefit from an array of athletic opportunities, including access to higher-level competition if appropriate and warranted.

The Middle School boarding program is a confidence builder. Our 8th grade boys will be prepared for leadership by their Upper School mentors, they will learn to problem solve and think critically by being encouraged to experiment, and they will build their character by having role models and teachers who are versed in Middle School needs.

Discover the YOU on your journey.

Our teachers know how boys learn best, so our classrooms are active and collaborative—you might build a model car, use physics to design a bridge, or act out Greek mythology. You’ll have access to all of our Upper School’s facilities, including our Arts Center, our Center for Learning Achievement, and our athletic fields. You’ll fine-tune your tech skills by using Chromebooks and taking classes on applied technology and robotics. A focus on study skills like note taking, time management, and test preparation will get you ready for success in the Upper School and beyond. And guess what? You’ll have a blast, and you’ll discover your journey is also one of life-long learning.

Your character is EVERYTHING.
What kind of man will you become?

Yes, you’ll learn advanced algebra. You’ll also learn how to carry yourself with honor and integrity. You’ll polish these traits in a community that asks you to ponder tough questions, like: Are you a man of your word? You’ll understand that being accomplished is about being thoughtful, caring, and empathetic.

Ready to see for yourself?
Dive in to Trinity-Pawling!

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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