SSL Certificate

Reunion & Homecoming 2018


*Subject to Change*

Friday, September 28

School Store Hours: 8:15 AM – 12:00 PM AND 1:00 PM – 4:00 PM

8:20 AM Open Classes

10:30 AM ALL ALUMNI Golf Game Quaker Hill Country Club 

11:00 AM – 1:00 PM Scully Hall open For Lunch

1:00 – 4:00 PM Registration and Welcome Center open Cluett Lobby

1:00 PM Is your son a prospective student? Student-led tours will be available at this time (*admissions interviews may be made by appointment)

4:00 PM Shuttle from Danbury hotels to campus 

4:00-7:00 PM Registration Open Cluett Lobby

5:30 PM Dedication of the Adams Erdmann Tennis Pavilion

*Reception to Follow

7:00 PM Welcome Dinner & Distinguished Alumni Awards

Your class photo will be taken at this event!

9:45 PM Shuttle to Danbury hotels


Saturday, September 29

School Store Hours: 8:30 AM – 12:00 PM AND 2:00 PM – 5:00 PM

7:30 – 9:00 AM Breakfast available Scully Hall

8:30 AM and 9:30 AM Shuttle From Danbury hotels

8:30 AM – 2:00 PM Registration and Welcome Center open Cluett Lobby

9:00 AM Clay shoot at Orvis Sandanona Shooting Grounds

9:00 AM Campus Tours by students of Key Club Cluett Lobby

10:00 – 11:15 AM Alumni Panel Gardiner Theater

11:30 AM Alumni Memorial Service All Saints' Chapel

12:00 1:30 PM Lunch and Alumni Celebrations Scully Hall

2:00 PM – Athletic Hall of Fame Induction Ceremony 1964 Alumni & Hall of Fame Room, Smith Field House

Athletic Events begin

2:00 – 3:00 PM 50th Reunion Class StoryCorps Barone Dining Room  

2:00 – 3:00 PM Guided walk on the Appalachian Trail Boardwalk Cluett Lobby

3:00 – 3:30 PM History of Trinity-Pawling Gardiner Library

BBQ Celebration (immediately following the football game)

Class of 1968 - 50th Reunion Dinner Gamage House

9:00 PM Shuttle to Danbury hotels 

10:00 PM Shuttle to Danbury hotels 

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.

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