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Just starting college, fresh out of grad school, first job, brand-new promotion, getting married, starting a’re all in different phases of life with one common bond: a shared link to Trinity-Pawling. You're our Young Alumni!


Alumni Hockey Game | Tirrell Rink | Saturday, December 1st | 1:00 PM

Candlelight Service | All Saints Chapel | Sunday December 10th | 5:00 PM

Boston Holiday Reception | Hosted by Peggy and Phil Haughey '53 | Harvard Club | Tuesday, December 4th | 6:00 PM

NYC Holiday Reception | Hosted by Jean Doyen De Montaillou and Michael Kovner '58 | Union Club | Monday, December 10th | 6:00 PM 

Young Alumni Reception | NYC | February 20th, 2019

Washington DC Reception | Hosted by Kathleen and Erik Olstein '86, P'11.'14,'17 | University Club | Thursday, May 2nd, 2019 | 6:00 PM

Contact Pete Lockwood for more information: 845-855-4881

Register for our gatherings at or (845) 855-4830


Being a Trinity-Pawling grad has its perks! The community is always available to you here and we benefit from your experience too. Simply because you are a T-P alum, you can:
  • Network with each other at regional events and in the Alumni Community app (you never know how you might land that next job!)
  • Catch up with favorite teachers during homecoming weekends.
  • Share what’s going on in your life!
  • Mentor students - you know best how the T-P experience helps boys navigate through college and career!
  • Support Trinity-Pawling to ensure current students have the same opportunities that you did.

Give Back

Speaking of support...
We know how often you’re asked to open your wallet for EVERYTHING, but hope you’ll consider Trinity-Pawling at the top of your list when you consider giving back.  Here’s why your gift, no matter the size, is important:
  • You’re paying it forward - All gifts to the Trinity-Pawling fund help preserve the school’s unique character and also support current students with scholarship funds and much-needed supplies.
  • You’re joining forces for the greater good - The more of you who contribute, the more you’ll strengthen your collective impact on every aspect of campus!

Your gift speaks for itself - Whether you give $10, $100, or $1,000, every gift counts and contributes to a robust alumni participation number.

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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