On Sunday May 7, 2017, Trinity-Pawling School may be hosting what will prove to be the largest gathering Pawling has seen in recent times! The Second annual “MayDay” is an event designed to raise awareness and money for two outstanding charities, Ryan’s Foundation, which is a non-profit designed to help kids in the Hudson Valley that have been diagnosed with cancer, and the Juvenile Diabetes Research Foundation, which funds research that transforms the lives of people with type 1 diabetes.

The event is extraordinarily inclusive, as all people from the greater Pawling area are invited to attend and enjoy a festive day on the Trinity-Pawling campus. Pawling will be buzzing on MayDay, as a wide variety of activities will be offered.

The main event remains a 2.2 mile “Extreme Cross Country” race. The race will wind throughout campus and will include two mud pits, water, hills and obstacles. Participants looking for a less physically demanding event can participate in a cross country style walk. Kids can also join us for a ½ mile race on the track. Other activities include an inflatable jousting ring, a dunk tank, a climbing wall and many other games of that nature.

New this year is a plant and flower sale, a student art sale, a large thrift sale and a cake auction. Lunch will be included with registration, and there will be food trucks on site as well to purchase extra food at an additional cost.

Registration will take place on the Trinity-Pawling campus on May 7, and all are welcome.  A full schedule and fee list will be released and posted on the school website in early April. MayDay is a spectacular opportunity to get involved in something great. For more information on MayDay 2017 contact Jay Kellogg at jkellogg@trinitypawling.org.

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 admissions@trinitypawling.org

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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