When I heard that I had to do a Senior Independent Project, I immediately thought how much fun it would be to do something that involves building an engine. I started brainstorming with our innovative art teacher Mr. Barnes, and we landed on the idea of restoring a scooter.

My next two challenges were finding a scooter and figuring out how to pay for it. I found a 1964 Vespa on Craigslist. That was the easy part. Figuring out a payment plan involved more creativity. I am involved in Relay for Life, so I asked our R4L advisor Mr. Mead if the club would front the money to buy the used scooter, and I would fix it up with Mr. Barnes. Once the scooter was restored, I would donate the scooter back to R4L to auction.  When I presented this idea to my advisor, everything fell in place.

Mr. Mead and I picked up the scooter in New Haven, and I took it straight to the maintenance barn. Although it started—it was in rough shape. With Mr. Barnes’ expertise and enthusiasm, this project has been a complete labor of love. I took the bike completely apart (even the engine), worked with a local body shop to help paint it (Thank You Dutchess Auto!) and am working with both the New York and Connecticut Relay for Life organizations to work out the plans to put this wonderful machine up for auction.

Stay tuned for auction details!

Matt Ernster ’18




The Alumni Ambassador program connects our students and our Alumni and provides opportunities for them to meet in person. “When an alum wants to know what Trinity-Pawling is like today, there’s no better source than a current student,” says Director of Major Gifts Colleen Dealy. She and Director of Stewardship Andy Busby Rickert ’81 created the program in 2013. Since then, Alumni Ambassadors have traveled to New York and Boston for yearly holiday events and play an important role in welcoming alumni back to campus during Homecoming and Reunion Weekend.

“It’s a highly selective group,” says Assistant Director of Alumni Programs Peter Lockwood ’10. “Until this year only a small group of boys were invited to apply, but this year anyone interested was welcome. We were really happy with the overwhelming interest, but we couldn’t take everyone.”

“What makes a good Alumni Ambassador isn’t necessarily what might make someone a Prefect, Proctor, or Dean’s Assistant. Candidates have to be comfortable in a social setting and able to walk up to an adult, introduce themselves, and carry on a conversation,” says Rickert ’81.

“Throughout the year, Alumni Ambassadors help out in the Alumni Office—don’t be surprised if you get a call from one of these boys—they help us get updated contact information and make phone calls in advance of events,” Lockwood explains.

The School holds its Alumni base in high esteem and wants current students to meet them in settings where they can discuss not only Trinity-Pawling, but professions and career choices. Hearing the exchange of stories between alums and current students is one of the best parts of the whole program.

This year’s Alumni Ambassadors are Mike McQuade ’18, Min Sang Ki ’18, Abdallah Bekhiet ’18, Brenden Lundy ’18, Brendan Simandl ’18, Geofrey Chu ’18, Mitch Bown ’19, Jack Haims ’19, Robby Phillips ’19, Will Rickert ’19, Phip Waugh ’19, Joe Musa ’19, and John Garvey ’19.  Aiden Pincombe ‘18 serves as the Head Alumni Ambassador.




During this season of Thanksgiving, I have pondered those things for which this Headmaster is grateful.


I am grateful for the opportunity to begin each school year anew.

I am grateful for the many ways that I learn from students and faculty.

I am grateful for the “can-do” spirit of students, faculty, coaches, and dormitory masters.

I am grateful for the trust of parents who have elected to send their son to Trinity-Pawling.

I am grateful for the support and fellowship of loyal alumni.

I am grateful for the vibrancy of new faculty who are beginning their career.

I am grateful to work at a school like Trinity-Pawling, where making meaningful differences in the lives of young men is our daily charge and where education is our life’s work and calling.

I am grateful for the good sense of humor and positive attitude of those around me.

I am grateful to those students who greet me each day and thank me after class, unaware of just how energizing those acts can be.

I am grateful when I see “old boys” helping “new boys” navigate the challenges of boarding school life.

I am grateful for the Trinity-Pawling faculty who consistently go the extra mile to help students grow and work toward their potential.

I am grateful to all those who work to “plant trees, under whose shade you do not expect to sit.”


Hand-made turkey created by the Trinity-Pawling faculty children.

Trinity-Pawling Middle School_Quad


We are excited to share news about the Trinity-Pawling Middle School:  boys don’t have to wait until Upper School to become a boarding student at Trinity-Pawling! A selection of 8th grade boys will be welcomed to join our boarding community each year.

The Trinity-Pawling Middle School curriculum is built on five themes that help boys gain a deeper understanding of their self-awareness, creativity, character and honor, and their place in an ever-changing world. With limited enrollment, the 8th grade boarding program is developmentally appropriate, individualized, and intentionally designed to nurture Middle School boys in preparation for the Upper School.

Students in the 8th grade will be engaged in a dynamic and comprehensive boarding school experience. Young scholars will immerse themselves in the boarding program and take part in a selection of vigorous programs which allow boys to experiment and explore:  arts & innovation, science & math, English language mastery, and cultural field trips. Boys will also be able to benefit from an array of athletic opportunities, including access to higher-level competition if appropriate and warranted.

The Middle School boarding program is a confidence builder. Our 8th grade boys will be prepared for leadership by their Upper School mentors, they will learn to problem solve and think critically by being encouraged to experiment, and they will build their character by having role models and teachers who are versed in Middle School needs.

With just 30 students in our Middle School, our small classes allow teachers to get to know the real boys. They will guide them on a journey of self-discovery to uncover their gifts and talents, and lay the foundation for future success.

Middle School students will have access to all of our Upper School’s facilities, including our Arts Center, our Center for Learning Achievement, and our athletic facilities. Boys will fine-tune their tech skills by using Chromebooks and taking classes on applied technology and robotics.  A focus on study skills such as note taking, time management, and test preparation will get students ready for success in the Upper School and beyond.

If you know a boy who would be a great fit for the 8th grade boarding program at Trinity-Pawling, contact JP Burlington at 845-855-4825.



Joe Alex ’96 returned to campus on a chilly November morning to give a Chapel Talk about what he feels is the most valuable takeaway from Trinity-Pawling: the concept of brotherhood. As a graduate of the Class of 1996, Alex spoke to the current students about the bond they will always share with one another—and the bonds they will form in the future. “You may not realize its significance right now,” Alex shared in his Chapel Talk. “But once you’re out, you quickly learn how lucky you were to be in the brotherhood.”

After graduating from Trinity-Pawling, Alex attended Adelphi University in Garden City, New York, where he studied Sports Management. He ambitiously entered the sports entertainment world, landing a variety of jobs, including working for the Olympics in Salt Lake City, the U.S. Open, and a sports radio station in Boston. The value of camaraderie that Alex experienced at Trinity-Pawling stuck with him through it all.

It was this concept of camaraderie, in fact, that led Alex to his drastic career change. In 2006, Alex left the world of sports entertainment and joined the family business, American Maintenance. “I saw the camaraderie that my dad had with my brother and I really missed it,” Alex shared. “That’s when I realized I wanted to be a part of it.”

American Maintenance is a full-service facility company, started by Alex’s father 44 years ago. Now as the company’s Vice President, Alex is grateful for his experiences in the Trinity-Pawling brotherhood that he continues to apply in his daily work. “T-P taught me structure and how to be resilient,” Alex explained. “But most importantly, it taught me about relationships. I learned how to socialize with more than just my peers. We lived with our teachers, ate dinner with our Headmaster—we had to know how to talk to them. I learned how to build relationships and communicate at Trinity-Pawling, which is so crucial in business.”

Alex stressed this importance of relationships in his Chapel Talk and he is hoping it resonates with the boys as they continue their time at the School. “Four years in the brotherhood go by quick,” he stated. “Soak it up, because there’s absolutely nothing like it.”



Jay Kellogg P’10, P’15, P’23 has been a devoted member of the Trinity-Pawling community for over 2 decades. As a teacher, advisor, parent, and head athletic trainer, Kellogg does it all. He gives each role the same attention and enthusiasm, enriching the School community as a result.

In late October, Kellogg’s hard work and dedication was recognized through the Arditti Fellowship Award. Each year, this endowed fellowship honors a member of the Trinity-Pawling faculty for “teaching excellence.” Criteria for consideration include outstanding knowledge of one’s academic field, commitment to our students and the educational program at Trinity-Pawling, and the inclusion of new teaching methods in the classroom. Members of the faculty nominate the individual who best exemplifies these qualities.

“A nomination that comes from the people you work with is something special,” Kellogg began. “In my eyes, being recognized by my peers is the greatest honor.”

As a recipient of the Arditti Fellowship, Kellogg was honored for his dedication in the classroom—and his most effective teaching method will not come as a surprise to those familiar with the Trinity-Pawling curriculum. Collaboration and active learning have been Kellogg’s go-to techniques since he first entered the teaching field. “I’ve been incorporating group work and active, out-of-your-seat learning for a long time,” Kellogg shared. “I believe in it and it’s so important when teaching boys. I’m very glad it has become such an essential part of the curriculum here at T-P.”

This year, Kellogg teaches Middle School science, 9th grade conceptual physics, 12th grade physics, and Sports Ethics. Through these classes, as well as his work as athletic trainer, Kellogg keeps the learning engaging, experiential, and completely hands-on. In Sports Ethics specifically, he is able to connect his lessons with his athletic training on the fields and courts. He also ties in real world issues and discusses how those issues may affect the boys in their not-so-distant futures. “It’s so valuable to have ongoing conversations with the students. One of the best lessons I try to teach is the value of listening,” Kellogg explained. “Athletic trainers are just as much counselors as we are trainers. We have to listen to the boys. I try to show them that adults can and do listen—and most importantly, we care.”

Though he juggles many roles at Trinity-Pawling, Kellogg reiterates one common message, and he hopes the boys hear it loud and clear before their time at the School comes to an end. “Above anything else, be inquisitive,” Kellogg advises. “Ask ‘why’ and don’t accept something just because it may be considered traditional theory.” Kellogg believes that this advice will lead to deeper learning experiences for both the boys and their educators, as they challenge one another to be curious and dive in. “I always say, we’ll learn a lot more from what’s between the lines than what’s between the book covers.”

Congratulations again, Mr. Kellogg, on winning the much-deserved Arditti Fellowship award!



You’re invited to join alumni, parents, and faculty for an evening celebrating the joy of the season with Trinity-Pawling School.


December 5, 2017 – 6:00 PM – 8:00 PM

Boston Holiday Reception

at Harvard Club of Boston

374 Commonwealth Avenue, Boston, MA

Hosted by Peggy and Phil Haughey ’53


December 10, 2017 – 5:00 PM

Candlelight Service at All Saints’ Chapel

Reception at Gamage House

700 Route 22, Pawling, NY

Hosted by Jennifer and Bill Taylor


December 13, 2017 – 6:00 PM – 8:00 PM

New York City Holiday Reception

at Union Club

101 East 69th Sreet, New York, NY

Hosted by Jean Doyen de Montaillou and Michael Kovner ’58


RSVP by email:

or call Janet Hubbard at 845-855-4830.




The Middle School soccer team concluded their season with an unbeaten record, their final victory coming over Dutchess Day School.

The 3rd soccer team had a terrific end to their season winning two of their last three games. The victories came over Gunnery and Salisbury. Jackson McAvoy ’21 provided leadership and good play in the midfield. Chris Devanny ’21 and Will Ackerman ’21 created a lot of offense and Lucas Hughes ’20 played well in the goal.

JV soccer concluded their season winning two and losing two in their final four contests. Victories over Millbrook and Salisbury moved the team closer to a .500 season.

The JV football team won their final contest of the season over Canterbury. The teams battled under the lights on a Monday afternoon and the Pride prevailed in overtime. Budd Desir ’20 had a touchdown on the final play of the game.

Varsity soccer had some exciting moments in the last weeks of the season. A draw against perennial power Hotchkiss was certainly a season highlight. Captain Marc Welch ’18 played an amazing game to keep the Pride close. One week later the team defeated an excellent Salisbury team and then earned a draw with Canterbury. Fahad Al Saud ’18 scored in three consecutive games. Captain Joe Webber ’18 was chosen All Star for both games.

The cross-country team competed in the Founder’s League meet and the New England Championships. Nick Grande ’19 was the Pride’s top finisher in both races.

The varsity football team concluded their regular season winning their final six contests. The highlight was an exciting come from behind win at Brunswick, where the Pride scored 19 points in the final five minutes. The running games of Chiz Umunawke ’18 and Ray Davis ’18 has been the catalyst in the winning streak. The second place finish in the Erickson League gave the Pride a spot in the Mike Atkins Bowl where Trinity-Pawling hosted Deerfield Academy. The Pride played a terrific defensive game, which led to a 23 – 7 victory. That win marked the seventh straight, giving Trinity-Pawling a record of 7 – 2.



Alumni, share your good news with your Trinity-Pawling friends! Please send in your Class Notes for the Spring 2018 Trinity-Pawling Magazine. The submission deadline is January 10, 2018!

Have you recently gotten married, entered retirement, welcomed a new baby into the family, embarked on a great trip, received a promotion at work, or won a community award? Let us know!

You can submit your good news online at

Questions? Contact Janet Hubbard P’07 by email at or call Janet at 845-855-4830.



Trinity-Pawling educates boys for life, instilling values that remain constant in an ever-changing world.

These values:  RESPECT – HONOR – INTEGRITY connect our community together and are the true hallmark of a Trinity-Pawling education.

When you contribute to the Trinity-Pawling Fund, you partner with others similarly dedicated to preserving the School’s distinctive culture and heritage. Your gift sustains and enriches all aspects of campus life and makes a difference for each and every student.

In a time when life moves too fast…will you help us ADVANCE what’s most important?

Discover giving options online at



Mark your calendar for Trinity-Pawling’s 14th Annual Golf Outing!

Once again, we are thrilled to be hosting our Golf Outing at Morefar Back O’Beyond in Brewster NY—considered by many to be one of the most exclusive courses in the country.

Stay tuned for more details about the 2018 Golf Outing. We can’t wait to see you on July 17, 2018!

All proceeds from the event will benefit the Trinity-Pawling Fund and the Miles H. Hubbard, Jr. ’57 Scholarship Fund. This scholarship was established to provide financial assistance to boys with exceptional athletic ability. Miles Hubbard served Trinity-Pawling as a teacher, coach, and athletic director for 37 years.



The MacGregor Robinson Endowed Chair for Mentoring is being named for MacGregor Robinson (1964-2017), one of the School’s most committed and generous educators. His life’s work was built upon the awareness that mentoring is one of the most meaningful gifts an educator can provide his or her students. He excelled in that role because he was blessed with many caring role models in his life.

It was MacGregor’s ambition to create a program at Trinity-Pawling that would be dedicated toward nurturing the mentoring skills of our faculty and staff as a means to further distinguish the School. This Endowed Chair for Mentoring was his vision and what he was working on in his final days.

In honor of MacGregor Robinson, donations may be made to this endowed fund, which will support professional growth to develop mentoring skills for faculty, and will specifically recognize educators at Trinity-Pawling who have demonstrated excellence in mentoring.

For details, please visit www.trinitypawling/macgregor  or contact Regan LaFontaine 845-855-4838.

Watch a video honoring the life of MacGregor Robinson.