SSL Certificate

Headmaster's Blog


Ventures on our Seas

In William Shakespeare’s Julius Caesar, Brutus says to Cassius, “On such a full sea are we now afloat that we must take the current where it serves or lose our ventures.” I have always been drawn to this statement and I remind myself of it often. At first glance, one could erroneously perceive a certain fatalism in the statement, a message that one has little control over one’s future. Far from suggesting powerlessness over events, Brutus is challenging Cassius to take advantage of the opportunities that present themselves. Of course, the saliency of the message needs to be removed from the deadly contexts of Shakespeare’s plot and the fate of Julius Caesar.

The wisdom of Shakespeare’s verbiage lies in the challenge that one must take full advantage of the circumstances that one faces, or else risk losing all that has been invested to date. Such wisdom has specific relevancy each day in the life of a school and in the process of teaching and learning. Learning and growth demand the exercise of certain healthy risks. If a student does not engage in the learning process with an initiative to learn what may seem unfamiliar and distant, then any learning will be superficial at best. Similarly, if a teacher does not engage each individual student in the learning process in challenging and dynamic ways, then his or her teaching will be diffuse and inefficient.

A teacher with integrity in his or her chosen profession chooses to teach because they have a desire to help young people grow toward a healthy, happy, and independent adulthood. In this context, dedicated teachers seek to take advantage of each opportunity that presents itself to help students grow and mature, both inside and outside of the classroom. To pursue this profession to its fullest extent requires tremendous investment, dedication, and patience. It requires that teachers take full advantage of each opportunity for a student’s learning and growth, recognizing that without such dedication the ventures of the profession will be met with less than positive results.

A school, if it is to take full advantage of the opportunities for the learning and growth of its students and its faculty, must cultivate and sustain a culture of connectivity. A culture of connectivity allows for relationships to flourish, especially those between teachers and students. A culture of connectivity creates a learning environment in which students feel comfortable taking healthy intellectual risks that will facilitate learning and growth. A culture of connectivity emphasizes the importance of respect in all that it does, including the ways in which it holds students accountable for their responsibilities.

Trinity-Pawling aspires to build and sustain a culture of connectivity to ensure that our pursuit of greatness is realized in the experience of our students. To paraphrase Shakespeare, it is on this sea that we are cast and we must take advantage of our vast opportunities to ensure that the goals of these ventures are not lost, but maximized. As we anticipate the rest of this and the next academic year, the faculty, staff, and I look forward to our partnership with you as we strive to reach the goals of our ambitions and ventures.


Posted by wtaylor on Friday April, 8, 2016 at 10:50AM

Choose groups to clone to:


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.

email page print page small type large type
powered by finalsite