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Friday, October 24

5:00-7:00pm : Registration and welcome center open (Cluett lobby)

5:30-7:00pm : Headmaster's welcome reception (tent behind Gamage House)

7:00pm : All-alumni clambake and lobster dinner (tent behind Gamage House)

Saturday, October 25

7:30-9:00 a.m. : Breakfast available (Scully Hall)

9:00 a.m. - 12:00 p.m. : Registration and welcome center open (Cluett lobby)

12:00 p.m. - 2:00 p.m. : Registration and welcome center open (McGraw Pavilion)

9:00 a.m. : Alumni chapel and memorial service (All Saints' Chapel)

9:30 a.m. (or immediately following Chapel Service) : Guided walk on the Appalachian Trail boardwalk (meet in Cluett lobby)
**activity level:easy

10:00 a.m. : Student-led campus tours, open classes, flag football game 

11:00 a.m. : Trinity-Pawling Today (Gardiner Library)                                                

Q & A with Headmaster Arch Smith followed by current students

12:30 p.m. : Alumni lunch and Hall of Fame induction (McGraw Pavilion)      

Inductees: T-P's 1964 football team and 1994 basketball team

2:00 p.m. : Guided historical tour of Pawling (meet in Cluett lobby)                       

Visit the John Kane House, Akin Free Library, and the Oblong Meeting House

2:30-6:00 p.m. : Homecoming games and alumni tailgates                                

Football: Coratti Field                                                                                         

Additional sports: list will be available on campus

5:30 p.m. : Headmaster's reception for all alumni (Gamage House)

6:30 p.m. : Reunion class dinners 

  • Old Guard (1926-1963), 1969, 1974 - Hosted by Gay and Arch Smith at Gamage House
  • 1964 - Dinner at Old Drovers Inn
  • 1984 - Hosted by Maria and Ned Reade at Reiter House
  • 1979, 1989 to 2009 and all non-reunion classes -  Oktoberfest Celebration hosted in Gamage Gardens


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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