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 Trinity-Pawling School
700 Route 22
Pawling, NY 12564
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Regan LaFontaine

Faculty Information
Department(s) Administration, Advancement
Title(s) Director of Advancement
Contact Information
Work Phone
Degree(s) B.A., Wesleyan University
M.A.L.S., Wesleyan University
Other Information

An alumna of Choate Rosemary Hall, Regan grew up in Marshall, Michigan before coming east. She received her B.A. in Government with a certificate in international relations from Wesleyan University, where she played varsity ice hockey and rowed on the crew team. She also earned her M.A.L.S. degree from Wesleyan with a concentration in Social Sciences.

Regan previously worked as a Senior Development Officer in Amherst College’s Office of Advancement. Prior to her tenure at Amherst, Regan worked as a Major Gifts Officer and as Associate Director of the Annual Fund at Wesleyan University. Regan has also worked in international educational programming for Elderhostel/Road Scholar, at Yellowstone National Park, and as a teen tour leader traveling throughout the United States. Regan’s most interesting occupation by far, however, is the year she spent as a “Hotdogger” traveling the hot dog highways of America in the Oscar Mayer Wienermobile.

In her free time, Regan loves traveling and has been to all fifty states and several countries throughout Africa, Asia, Europe, and North America. She enjoys playing ice hockey and other sports, outdoor activities, and creative endeavors.

Regan and her husband, Nick, live in Dunbar North with their son Lincoln and daughter Sawyer.

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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