SSL Certificate

The new school year is just around the corner! Whether you're new to the Pride or a returning student, these resources will help you and your family prepare for the upcoming academic year. Please check back throughout the coming weeks for frequent updates. If you have any questions or concerns, please reach out. We're looking forward to another great year at Trinity-Pawling!

Welcome Letters to Parents

An introduction to the new school year from Trinity-Pawling's Dean of Students, Josh Collins ’95. Please feel free to reach out with questions.

Move-In Dates

Registration will be in the Smith Field House.

Varsity Football and Varsity Soccer Candidates Arrive
Registration from 10:00 AM to 12:00 PM

Cross-Country Runners Arrive
Registration from 10:00 AM to 12:00 PM

Seniors, PG's, & New International Students (Non-North American) Arrive
9:00 AM to 11:00 AM

New Underclassmen Arrive (Day and Boarding)
9:00 AM to 11:00 AM

Returning Underclassmen Boarding Arrive
2:30 PM to 4:00 PM

Returning Day Students Arrive (Grades 9-12)
3:00 PM to 4:00 PM

Middle School Orientation
9:00 AM, Dann Courtyard

Early Sports Tryouts

Early Sports Tryouts: Fall 2018
Soccer & Football: Saturday, September 1st; Registration from 10AM-12PM
Cross Country: Tuesday, September 4th; Registration from 12PM-2PM

Please select your sport and complete the accompanying form to sign up for Early Sports Tryouts for the Fall 2018 Athletic Season.

Can't Make It? Don't Sweat It!
For those not able to make it to Early Sports Tryouts, below are the Opening of School move-in dates. You will still be able to tryout for a varsity team even if you miss Early Sports.

  • Wednesday, September 5th: Seniors, PGs, and new international students (non-North American)
  • Friday, September 7th: New and returning underclassmen

Questions? Reach Out!
Jim McDougal, Cross Country Head Coach
Nick LaFontaine, Football Head Coach
Sam Clougher, Soccer Head Coach

2018-2019 Calendar

Here is the yearly calendar for the 2018-2019 school year.

Purchase Books

To purchase books for your courses, please visit MBS Book Store online. Be sure to have your books delivered to Trinity-Pawling School (700 Route 22, Pawling, NY 12564)

A few tips:

  • We release academic schedules in early August. Please be sure to have a copy of your schedule handy when purchasing your books.
  • Make sure to order the exact book; if you use another vendor, use the ISBN number to verify.

What to Wear

Still finishing up your school clothes shopping? Check out our What to Wear video to make sure your closet is stocked with the right items! 


Community Handbook

We publish an updated version of our Community Handbook every August. Please be sure to read through the handbook before the start of school to ensure a positive and productive year at Trinity-Pawling.

Suggested Packing List

This Suggested Packing List is provided to assist all boarding students and parents in preparing for the upcoming school year.

Dorm Information

You should receive your dorm assignment in early to mid-August. This updated Dorm Guide is provided for all boarding students and parents to prepare for their boarding experience. Below is additional information on each specific dorm on campus. If you have any questions, please reach out to Dutch Keel, Dean of Residential Life.

Day Students & Driving

Please take note of the School's Expectations & Car Policy for all day students. Students are required to complete two forms if they are planning to drive to and from campus at any point during the school year: (1) Vehicle Registration Form and (2) Vehicle Procedures Agreement

If you have any questions, please reach out to Josh Collins ’95, Dean of Students.

Off-Campus & Weekend Procedures

Below are informational documents regarding weekend privileges, transportation to and from campus, school vacations, and other off-campus procedures. Please take the time to understand the School's policies on students' off-campus privileges throughout the school year.

If you have any questions, please reach out to Josh Collins ’95, Dean of Students.

Computers & Technology

All students are required to complete and submit an Acceptable Use Policy Form before arriving for the Opening of School. Please sign, scan, and return the form via email as soon as possible to Bryan Turner, Director of Technology.

Business Office Basics

Below is a list of Business Office forms that parents will need to complete before the beginning of the school year. If you have any questions, please visit the Parent Portal or contact the Business Office at 845.855.4815.

  • Tuition Refund Insurance Waiver Form (Please note: All students are automatically enrolled in TRI when a signed contract is received by the School.  The premium appears on the first tuition statement and you have an opportunity to waive coverage if not desired.)
  • Health Insurance Election Form (Please note: Students residing in the United States may enroll in any of the Student Health Insurance Programs by completing the Student Health Insurance Form and returning it to the Business Office with payment.)
  • Health Insurance Waiver Form (Please note: International students are enrolled in the Student Health Insurance Plan I, 12-month program. Parents opting out of the program must submit a waiver form by September 1st and provide proof of a United States based Health Insurance Company.)
  • Accident Insurance Waiver Form (Please note: This program reimburses for medical expenses that arise from an accident in which a student is injured. The premium appears on the first tuition statement and you have an opportunity to waive coverage if not desired.)

MyKidsSpending & T-P Card

The T-P Card is a convenient, prepaid money management debit card account which allows the student to enjoy School Store and Cave purchasing power, as well as access to cash. 

All students are required to have a T-P Card. The card serves as the student ID card and the Gardiner Library Card, as well as grants access to the School Store and Cave. The advantage to the T-P Card is the student never needs to carry cash on campus. 

Complete the T-P Card worksheet and mail it along with a deposit to the Student Accounts Office. To activate the T-P Card, it is suggested a deposit of $2,000 for international boarding students, $1,000 for domestic boarding students, $500 for upper day students and $300 for middle school students be made to open the account. There is a $20 set up fee for all new students.

MyKidsSpending is another way to add money to your students' T-P Card and track their spending online. To enroll in MyKidsSpending, visit and create an account. You will need the 4-digit code on your tuition statement to create an account.

To learn more about setting up a T-P Card and/or MyKidsSpending Account, visit the Parent Portal. Questions? Please contact the Business Office at 845.855.4815 or

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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