SSL Certificate



Presented by Headmaster William W. Taylor

The Dunbar Award for Service is given each year by Bill and Helene Dunbar who spent more than 30 years at Trinity-Pawling as Assistant Headmaster and librarian respectively. Not long after their retirement in 1978, the Dunbar Award for Service was created to honor their service to the School and to recognize those members of the community, be it a student, a faculty member, a spouse, a staff member, or a friend who served the School with the same steadfast devotion. Louis Sam Inghilterra

French Laurence Webber

Spanish Matthew J. Cerny

Anderson Prize in Latin Zhou Sun

Art Hitoshi Matsukage AND Vu Tien Minh Nhat

Instrumental Music Award William Francis Estony

Vocal Music Award Zi Dong (Jackson) Wang

The Tennant Drama Award is donated each year by Mrs. John S. Tennant whose sons graduated in 1950 and 1954. Four of her grandsons are also Trinity-Pawling graduates. Ira Daniel Conklin IV AND Hunter Brennan Olstein

Henderson Prize in English Ryan M. Winn

Archibald A. Smith III Mandarin and Chinese Studies Award Kenneth C. McDougal

Frederick Douglass and Susan B. Anthony Award 
Humanities/Social Science Award Benjamin Holmes Girolamo

Environmental Science Award Christopher Michael Connolly

Mayflower Award Jack Elio Irwin

Excellence in History (Senior) Kenneth C. McDougal

Colhoun History Essay Prize Marc Gregory Welch

Religion Award Zhongwen Zhang

Elliot Prize in Senior Mathematics Zhou Sun 

Biology Award Yunpeng Li

Chemistry Award Matthew Gaston Galarza

Rensselaer Medal Xiangjin Zhang

Bausch and Lomb Award Junhan Yan

Ernest J. Reiter Award for Physical Science Glyn Ge 

The Norwood L. Pinder Prize for Excellence in Journalism was established in 2006 to recognize at Commencement the outstanding contributions of a student to the journalistic enterprise on campus. Named after the first editor of The Phoenix in 1908, the original literary journal and yearbook of the Pawling School, this prize honors Pinder's legacy of giving voice to the life of the School.  Hunter Brennan Olstein

Excellence in Theater Nathan Christopher Tanner

Penn Book Award Joseph Henry Webber

Harvard Prize Book Nathan Christopher Tanner

George Eastman Young Leaders Award Charles Michael Csaszar

Xerox Award for Innovation and Information Technology Jie Wen

RIT Computing Medal Award Geoffrey Shing Hei Chu

St. Lawrence Book Award Ryan Zachary Devanny

Saint Anselm College Book Award Aiden Cole Pincombe

Outstanding Achievement in Junior Global Collaborative Project Connor Thomas Bastidas, Charles Michael Csaszar, Ryan Zachary Devanny, Marc Gregory Welch, AND Jie Wen

Outstanding Achievement in Senior Independent Project Ronald Joseph DiMaggio

The Creighton E. Gatchell Sportsmanship Award, donated in memory of Creighton, class of 1961, by his brother Bill, a member of the class of 1963, is given to a member of the senior class who best exemplifies Creighton's love for sports and his level of sportsmanship. Christopher Thomas Taylor

The Kenneth B. Weeman Athletic Award is given by his widow and sons, members of classes in 1959 and 1961, and his grandson, a member of the class of 1991. Factors to be considered are the individual sense of sportsmanship, demonstrated leadership, personal commitment to the athletic program, and to the traditions of Trinity-Pawling School. Jeffrey Edward Thompson

Honor Student in Each Class:

  • Freshman Yuanlun Xu
  • Sophomore Robert Frederick Phillips
  • Junior Xiangjin Zhang
  • Senior Ryan M. Winn

Colhoun Award to Most Improved Freshman Ignacio Fomperosa 

Hastings Award to Most Improved Sophomore Jackson Andres Breton

Citizenship Awards: Citizenship is like art; it is hard to describe but we all know it when we see it. Citizenship is that ability to be thoughtful, helpful, patient, kind, respectful, and courteous...all in the right amount, at the right time, and with the right amount of sincerity. 

  • Freshman (Duncan Pyle ’86) Henry Daniel
  • Sophomore (Scott Carlin ’11) John Michael Garvey
  • Junior Charles Michael Csaszar
  • Senior Louis Sam Inghilterra

Kevin Neal Acrish Award Ryan M. Winn

The McCollum Award is named for the first Head Prefect of Trinity-Pawling, Franklin McCollum, class of 1950. Mr. McCollum never forgot the lasting impact that Trinity-Pawling had on his life and that of his classmates. To be Head Prefect is even more demanding as all of this has to be done with the added burden of knowing what to say and what to do while leading the class of 2015 each day. Jack Thomas Makris

Valedictorian for the Class of 2017 Ryan M. Winn

Headmaster’s Award for Excellence Jonathan Isaiah Girard

The Wells Award, named for its donor, a member of the class in 1938, is presented annually to the student who combines outstanding performance and growth in all areas of life at Trinity-Pawling School. Character, a concern for and service to others, loyalty and dedication to the established traditions of the school are among the criteria for determining the award. Jeffrey Edward Thompson

Matthew E. Dann Award for General Excellence. Dr. Matthew E. Dann was headmaster of Trinity-Pawling School 1946 to 1970. This award is given annually by his family and friends recognize the outstanding boy in the junior class. Joseph Henry Webber

Eugene O. Colley Award for Leadership. Gene Colley has been involved with Trinity-Pawling School for more than 30 years as a parent of four graduates and since 1978 as a trustee. Long before he had an official role in school, in his typical fashion of "getting the job done", he commandeered the necessary forces to restore electricity to the campus after the 1969 fire which nearly leveled the south end of Cluett. Without Gene's leadership, the school would have closed for a year or perhaps longer. "It cannot be done" is not a phrase which he cares to hear. Jeremy Alexander Wilson

Gamage Award for General Excellence. The Gamage Award, named for Frederick Luther Gamage, founder and first headmaster of the Pawling School, is awarded by vote of the faculty to a member of the senior class whose overall record is one of General Excellence. Ryan M. Winn

Congratulations to the following recipients of the 2017 Phil Haughey ’53 Three Varsity Sport Award: Tre Fletcher '20, Zack Conlan '19, Jake Conlan '19, Joe Perettine '18, Joe Webber '18, Joey Musa '19, Connor Bastidas '18, Nate Tanner '18, Zach Mazur '17, Hitoshi Matsukage '17, Dennis Ilmela '17, Stephen Morrissey '17, Chris Taylor '17, Will Dencker '17, Jeff Thompson '17, Avery Johnson '17

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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