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Headmaster's Blog


Leaving the Harbor

My brother and I grew up on the water and learned how to sail when we were kids. Sadly, my sailing skills never progressed passed the ability to sail a Jayhawk sailboat on the Long Island Sound; I became a proficient member of any sailing crew, however. My brother, on the other hand, became an accomplished sailor. He lives on the coast of Maine and spends his brief summers sailing his wooden sailboat, Navajo, around the Northeastern coast.

While I lack his sailing acumen, I often find myself using nautical imagery in my references to the life of a school. This time of year, for example, I find myself talking about getting the boat out of the proverbial harbor. I love the beginning of a new school year because it is the beginning of a new and somewhat unpredictable journey. Toward that end, I think a water journey is an apt metaphor for the school year and education in general.

Water symbolizes life. A sailboat, moreover, is not built for the safety of harbor. A boat’s journey through the water is characterized by various stages of challenge. So it is with growing up; so it is with the life of a school. The school year is a journey for students, parents, and teachers. Each year, there are times of smooth sailing and there are times of rough water. Sailboats, much like schools, are built for the rough waters that inevitably accompany any journey.

For students, teachers, and parents, periods of calm waters allow for a much needed respite on the journey. A sailboat, however, doesn’t move very well in calm waters. It may be peaceful for a time, but the sailing will quickly turn tiresome and, ultimately, unproductive. You need wind and friction to move productively through the water and take you toward your planned destination.

To sail, you don’t just aim your sites on your ultimate objective and then set out on your journey. Sailing involves learning how to tack, how to traverse from one direction to another in a way that efficiently captures the wind in the sail. In sailing, taking the direct path between two points will not be the most effective or efficient means to reach your destination. Instead, you must traverse while moving forward. The same is true for young people on their journey through school.

As parents and teachers, we may want our children and students to move unwaveringly toward the objectives we have set out for them. This never happens, however. There are always changes in directions as they move toward their destination. As young people grow older, moreover, it becomes increasingly important to let them take the till and steer the boat with our guidance. As such, their destination and the one that we have envisioned for them may end up being slightly different. Yet, by learning to tack and capture the wind behind them, their destination is never very far from the one that was envisioned when the boat left the harbor.

So, as we begin another school year, I also think of the larger ship known as Trinity-Pawling. The ship has some new members of its crew, some upgrades to its structure, and some additional passengers. Its cargo, though, is as ever precious and prized as it always has been. Its ultimate destination, however, is envisioned in its mission. During the course of this journey, boys will become young men as they discover the potential for greatness that exists in each of them. They will further explore their distinctive gifts and talents, assisted by caring faculty and a camaraderie of brothers. To be sure, the turbidity of the waters will change from time to time on the journey. Time must be devoted to tack when necessary so to fully capture the wind that will direct this journey.

I look forward to the sail and to the journey that will lead us to a new harbor come next June. Onward!

Posted by wtaylor on Thursday September, 17, 2015 at 02:27PM

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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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