Open Houses & Events

Sat., November 07, 2026  - Pawling, 

Open House
Trinity-Pawling School
700 Route 22, Pawling, 12564, USA
9:00am (EST) - 12:00pm (EST)

RSVP needed: Yes - Register and get more information
Further information: Office of Admissions, (845) 855-4825, [email protected]

We hope you'll join us on campus for our Admissions Open House on November 7, 2026! Experience Trinity-Pawling School at our Open House! Connect with students, faculty, and coaches, and see firsthand the brotherhood, energy, and traditions that make our School exceptional. Registration is required.

Mon., November 09, 2026  - Pawling, NY

Virtual Event
Trinity-Pawling School
7:00pm (EST) - 8:00pm (EST)

RSVP needed: Yes - Register and get more information
Further information:

Exploratory Learning: Curiosity, Discovery, and Self-Awareness in Boys' EducationHow do boys become curious and confident learners? This panel discussion examines how Trinity-Pawling's learning environments and experiences enable our students to explore and discover their gifts and talents. We'll look at how Trinity-Pawling creates opportunities that encourage curiosity, healthy risk-taking, collaboration, and greater self-awareness. Join Head of School Bill Taylor, faculty, and students for this important conversation.

Wed., January 06, 2027  - Pawling, NY

Virtual Event
Trinity-Pawling School
9:00am (EST) - 12:00pm (EST)

RSVP needed: Yes - Register and get more information
Further information:

Making Learning Relevant for Boys What makes learning meaningful and motivating for boys? This panel discussion explores how Trinity-Pawling engages boys through five essential elements: Challenge, Autonomy, Effort, Relationships, and Purpose. We'll look at how boys learn differently and how that shapes the way we teach and think about engagement across all aspects of life at the School. From active classrooms and experiential learning to movement and athletics, we'll explore how opportunities to move, collaborate, take ownership, and connect learning to real-world purpose support boys' growth in the classroom and beyond.Join Head of School Bill Taylor, faculty, and students for this important conversation.

Wed., February 24, 2027  - Pawling, NY

Virtual Event
Trinity-Pawling School
7:00pm (EST) - 8:00pm (EST)

RSVP needed: Yes - Register and get more information
Further information:

AI and the Human-Centered Learning Experience at Trinity-PawlingWhat do boys need to thrive in a rapidly changing world? This panel discussion explores howTrinity-Pawling is approaching AI as a tool to enhance learning while keeping the human experience at the center - cultivating curiosity, critical thinking, relationships, and character development.Join Head of School Bill Taylor, faculty, and students for this important conversation.