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Headmaster's Welcome

Headmaster Bill Taylor

This will be an exciting year of growth at Trinity-Pawling! 

Our theme for the school year is “Engaging the World.” In an increasingly interconnected world, it is vital for our students to engage the world so that they can become leaders and active contributors to society. Students must be engaged if they are to be leaders; they must be engaged if they are going to be creative problem-solvers; and they must be engaged if they are going to allow their God-given potential for greatness to be realized. Critical thinking will define this engagement at Trinity-Pawling and will best prepare our students to navigate a world where information is increasingly mistaken for thought. 

While the ethos and mission of Trinity-Pawling has remained consistent over the years, education is changing rapidly. There is a paradigm shift occurring in the world of education that is forcing changes in the ways that material is taught and learned. Students must learn critical information. Increasingly, though, value is placed on how students will be able to apply and convey this information in creative, collaborative ways. Not only is it important for students to be prepared to know the answers to important questions, increasingly they must learn how to ask probing questions that reveal new opportunities for meaning and insight.

Trinity-Pawling is moving forward to respond to the changes occurring on the educational landscape. Specific focus is being directed toward project-based learning and ways that we can incorporate more innovation into the curriculum.  Our faculty is focusing on inquiry-based learning, rather than transmissive teaching. Moreover, enhanced focus is being directed toward experiential education and teaching entrepreneurial skills.

The learning environment at Trinity-Pawling guides students toward greater self-awareness through the relational trust that characterizes this community. Here, there is room for boys to explore interests and pursue passions in a learning environment that encourages healthy risks and supports them in this process. This community continues to search for those spaces where a boy can immerse himself in discovery. I believe that Trinity-Pawling is distinctively and deliberately poised to prepare our students for leadership in an ever-changing world.

It is an exciting time to be an educator at Trinity-Pawling!  We look forward to sharing this journey of learning with you.


William W. Taylor



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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