Trinity-Pawling is proud to launch the 2025–2026 Pride Perspectives webinar series this October — a dynamic platform designed to keep our community informed and connected to the School’s core mission of educating and empowering boys. Building on strong engagement from past years, this season will take a deeper look at the state of boys’ education, positioning Trinity-Pawling as a leading voice on the challenges and opportunities facing young men today.
The first webinar, “Boys, Boarding School, and the Loneliness Epidemic,” will take place on Monday, October 20, at 7:00 PM. Head of School Bill Taylor will lead a thought-provoking conversation with Trinity-Pawling faculty, exploring the growing crisis of isolation among boys and how a boarding school environment can be a powerful antidote. Together, they will discuss how Trinity-Pawling’s expertise in boys’ education, culture of mentorship, and close-knit community help students move beyond loneliness to build meaningful friendships, confidence, and a true sense of belonging.
Parents, alumni, and friends of the School are invited to join this timely discussion and discover how Trinity-Pawling’s programs foster connection and resilience in boys. Whether you are a current family or simply curious about the boarding school experience, this webinar offers valuable insight into how Trinity-Pawling prepares young men for lives of purpose and leadership.
Register on Zoom to be part of this important conversation — and help us kick off another exciting year of Pride Perspectives!