Trinity-Pawling Headmaster Bill Taylor

During a recent Preview Day presentation, Headmaster Bill Taylor encouraged visiting families to take a “deep” look at the schools they would be visiting. “One should look for the “soul” of a school,” said Taylor. He explained that many schools have outstanding facilities and ambitious curriculums and are situated in beautiful environments, but the “soul” of a school is what cannot be seen on the surface. “The soul of a school is revealed in its community — it is what allows students and faculty to develop their self-awareness, it is a community that encourages stepping out of one’s comfort zone to build self-reliance, it is a community that is supportive and caring — one that builds meaningful relationships with one another,” said Taylor. These are the qualities of a school, which determines its depth as an institution.

“As time goes by, I increasingly appreciate what an influence Trinity-Pawling had on my development as a person” — this is a phrase we hear often as our alumni share stories of their time at Trinity-Pawling — it is one of many examples of the “depth” of the Trinity-Pawling experience. “Many of the seeds being sown at Trinity-Pawling are not intended to germinate until after boys graduate, when they have the maturity to fully appreciate what the experience has fully meant to them,” explained Taylor. “These seeds grow deeply inside the experience of our students and provide a lifetime of reflection and guidance.”

“The irony is, we think we don’t need structure when we are teenagers, but that is what we crave most. It is the single greatest gift that Trinity-Pawling gives us forever,” stated alumna Allison Whipple Rockefeller ’76, who attended Trinity-Pawling during its brief period as a co-ed school. “It is the foundation of the life I live today, one of discipline and expectation for myself.”