Meet the Head of School

A portrait of Headmaster Bill Taylor at Trinity-Pawling School
Head of School Bill Taylor 

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, yet more 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 also learn how to ask probing questions that reveal new opportunities for meaning and insight.

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. Our faculty is focused on inquiry-based learning, rather than transmissive teaching — towards experiential education and teaching entrepreneurial skills. 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 and a student at Trinity-Pawling! We look forward to sharing this journey of learning with you. Onward!

The Power, Potential, and Promise of a Counter-Cultural Education

During a special Parents' Weekend presentation in Gardiner Theater 0n October 20, 2023, Head of School Bill Taylor spoke to families about how Trinity-Pawling addresses the issues of today’s culture and why this “counter-cultural” approach is vital for the future.

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"By challenging the norms, Trinity-Pawling is shaping future leaders who will thrive in the ever-changing landscape of the modern world."

Head of School Bill Taylor

Bill's Blog