Reunion Weekend 2025 takes place on October 3-4, 2025, honoring class years ending in 5s and 0s — it’s almost here! This special occasion brings together alumni from across the decades to reconnect, reminisce, and celebrate the enduring bonds of the Trinity-Pawling community.
Homecoming and Reunion Weekend is one of our most cherished traditions, providing an opportunity for alumni to revisit campus, reconnect with classmates, and witness the growth of the School firsthand. Whether it’s strolling through the historic campus, cheering on our athletic teams, or attending special class gatherings, there’s something for every Pride member to enjoy.
This weekend is not just about looking back; it’s about celebrating the present and inspiring the future. Alumni will have the chance to meet current students and faculty, hear updates on exciting school initiatives, and share stories that highlight the lasting impact of their Trinity-Pawling experience.
From spirited events on campus to intimate class dinners, Reunion Weekend promises a mix of nostalgia, laughter, and meaningful connection. It’s a time to honor the legacy of your class, celebrate achievements, and strengthen the lifelong relationships that make our community so extraordinary.
We look forward to welcoming you back to campus for a Reunion to Remember! Don’t miss this opportunity to celebrate your time at Trinity-Pawling and create new memories with the Pride.
Here’s the full schedule:
Friday, October 3, 2025
School Store Hours: 8:30 – 11:30 AM and 12:30 – 6:00 PM
10:00 AM – 3:00 PM: All-Class Reunion 18-Hole Golf Outing, Salem Golf Club
3:30 – 5:00 PM: Alumni Hockey Game and Class of 1973 Zamboni Dedication, Tirrell Hockey Rink (Dependent on Rink Conditions)
3:00 – 6:30 PM: Registration and Welcome, Cluett Lobby
6:00 – 6:30 PM: The Trinity-Pawling Experience Student Panel with Head of School Bill Taylor, Gardiner Learning Commons
6:30 – 8:30 PM: All-Alumni Welcome Reception, Scully Dining Hall
7:30 – 9:00 PM: 35th Reunion Dinner for the Class of 1990, Gamage House
Saturday, October 4, 2025
School Store Hours: 9:00 AM – 3:30 PM
9:00 AM – 3:30 PM: Registration and Welcome, Cluett Lobby
9:30 – 10:45 AM: Honor Guard Reception 1942-1975 and Distinguished Alumni Awards – Moderated by Head of School Bill Taylor, Gardiner Theater
11:00 AM – 12:00 PM: Alumni Memorial Service, All Saints’ Chapel, including a tribute to Ted Kneeland
12:00 – 1:00 PM: BBQ Lunch, Scully Dining Hall
1:15 – 2:45 PM: Athletic Hall of Fame and Arts Hall of Fame Induction Ceremony, Gardiner Theater
3:00 – 6:00 PM: Homecoming Football Game, David N. Coratti Field
*Please be aware: According to the NEPSAC Code of Ethics and Conduct, the use of alcohol and illegal drugs should not be associated with any athletic event on campus.
6:00 – 7:30 PM: All-Alumni Farewell Reception with Refreshments & Hors d’oeuvres, Smith Field House Terrace
7:00 – 9:00 PM: 55th Reunion Dinner for the Class of 1970, Barone Dining Room
7:00 – 9:00 PM: 50th Reunion Dinner for the Class of 1975, Gamage House
If you haven’t done so yet, RSVP today and join us for this special weekend of tradition, camaraderie, and celebration!
This spring, Head of School Bill Taylor, his wife Jennifer, and Director of Advancement Elly Erickson embarked on a special journey to Asia, where they were warmly welcomed by members of the Trinity-Pawling community. Over the course of five gatherings in China, Japan, and Korea, more than 125 alumni, parents, and students came together to celebrate the shared bonds that unite us across continents. The visit provided a wonderful opportunity to reconnect, strengthen friendships, and look ahead to Trinity-Pawling’s bright future.
At every gathering, the Taylors and Ms. Erickson witnessed the deep reach and lasting influence of a Trinity-Pawling education. One of the most profound aspects was how alumni living abroad embraced current and future students. New students — even before setting foot on campus — were welcomed into the Pride by their peers and graduates of the School.
“It was truly special to reconnect with so many alumni and students at the Seoul Reception—thanks to the School’s incredible effort,” shared Joon Sung Kim ’04. “Bill Taylor’s presentation was a powerful reminder of how much Trinity-Pawling has grown and how connected we still feel to the teachers and community that shaped us. I really hope more alumni take part in future events like this — you’ll be glad you did.”
Director of Advancement Elly Erickson echoed this sentiment. “In Seoul, a large circle of alumni opened up to include both current and incoming students. Watching them warmly welcome the next generation into the Trinity-Pawling community was inspiring and embodied the enduring values of a TPS education.”
In Tokyo, Yu Tamura ’10 highlights, “Of all the invaluable lessons and experiences I gained at Trinity-Pawling, the greatest gift has been the lifelong connection with my TPS brothers across generations. The gathering in Tokyo truly reminded me of the strength of these bonds. I look forward to staying connected and contributing to the future growth of this amazing community.”
Guests at each event expressed deep gratitude for the School’s outreach. “We are deeply grateful to Trinity-Pawling School for this Asian visit opportunity, which has given us parents in Shanghai a precious annual gathering moment,” comments Mr. Jing Zhou and Ms. Yinzhi Han P’28, William’s parents and hosts of the Shanghai gathering. “This connection not only promotes the children’s mutual assistance, cooperation and growth performance on campus, but more fortunately, the children were also present when Mr. Taylor visited this year. This undoubtedly makes the bond between parents and the School closer and deeper, and such interactions are of great significance to the development of the community and the children.”
The receptions also featured enriching cultural experiences. In Shanghai, guests enjoyed a private tour of the Han Tianheng Art Museum, guided by William Han ’28, who recounted his family’s heritage with the museum and stories behind its art treasures.
As part of the Beijing Reception at the CP Center—an esteemed landmark that serves as a vital platform for dialogue and exchange among Chinese business leaders around the world—reception guests were invited to experience the Center’s remarkable Grand Hall. Encompassing more than 4,500 feet in a panoramic, multi-sensory design, it stands as the largest and most distinctive venue of its kind in China.
Beijing Reception hosts Mr. Ping Tse and Ms. Yanxia Zang P’29 share, “We were delighted to host the event in Beijing because we deeply believe in the School’s mission and vision. Supporting this visit was our way of contributing to a stronger, more connected community—which we see as essential to the School’s continued growth and excellence. It was especially meaningful for our families to hear directly from Mr. Taylor and feel even more inspired about the future we’re building together.”
Head of School Bill Taylor expressed his appreciation for the extraordinary hospitality shown at every stop. “We extend our heartfelt gratitude to the many families and alumni who contributed to these memorable gatherings. Their participation made this journey especially impactful. From stunning venues to seamless logistics, each detail reflected the gracious hospitality and dedication of our worldwide network of families and friends.”
Special thanks go to the generous families and alumni who helped make this journey a success:
● Shenzhen, China: Mr. Jinchao Huang and Ms. Xiaowen Zhang P’27
● Shanghai, China: Mr. Jing Zhou and Ms. Yinzhi Han P’28
● Beijing, China: Mr. Ping Tse and Ms. Yanxia Zang P’29
● Tokyo, Japan: Yu Tamura ’10 and Sugako Maeda P’23
● Seoul, Korea: Nam Kyu Kang ’97, Joon Sung Kim ’04, and Jay Choi ’15
Kudos also goes to our student translators — Bohen Hu ’26, William Han ’28, Akina Tse, and Shun Shiraishi ’23 — for their invaluable support.
These gatherings were filled with camaraderie and an inspiring sense of joint purpose. Whether reminiscing about campus days, exchanging stories of current student life, or envisioning the School’s future, the spirit of Trinity-Pawling was present in every moment.
The Pride’s global family continues to grow stronger. To attend, coordinate, or assist with future events in Asia, please contact Elly Erickson at eerickson@trinitypawling.org or via WeChat (ID: TPS-Advancement). Together, we are building bridges that unite our international community and fuel the thriving future of Trinity-Pawling.
Each spring, the Trinity-Pawling community gathers for the Stepping Up ceremony, a cherished tradition where rising seniors are chosen to serve as Prefects for the year ahead. The title “Prefect,” derived from the Latin word for “leader,” is a distinction earned through the respect of both peers and faculty. These young men embody Trinity-Pawling’s core values of honor, respect, and hard work.
On May 23, 2025, seven students were elected as Prefects for the 2025–2026 school year, recognized for their leadership and dedication to the School community. As the new academic year began in September, Head of School Bill Taylor welcomed the group to Gamage House for a dinner and conversation about their roles, responsibilities, and opportunities to lead. Each Prefect has been entrusted with a specific area of oversight, detailed below.
Here’s a look at the 2025–2026 Prefects:
Arthur Figueiredo, Head Prefect
● Hometown: Brewster, MA
● How many years have you been at Trinity-Pawling? Three years
● Interests/Hobbies: Playing baseball, hockey, soccer, and golf, spending time with friends, and reading.
● What is on your senior year bucket list? Make the Head of School list.
● What is your secret talent? I am a decent sports action photographer.
“Being a Prefect is setting the example of being open and friendly, working hard, and having determination at whatever you do. Being a Prefect is naturally setting an example for the entire community.”
Axel Caramico, Junior Prefect of Honor
● Hometown: Poughkeepsie, NY
● How many years have you been at Trinity-Pawling? Six years
● Interests/Hobbies: Soccer, wrestling, theology, reading, and philosophy.
● What is on your senior year bucket list? Go far in spooning, participating in a school play, and improving club life at T-P.
● What is your secret talent? I can kickflip on a Tech Deck.
“Being a Prefect to me means actively trying to be a model student at T-P through all aspects of life and taking the initiative to better the community as a whole.”
Chase Laramee, Prefect of Connections
● Hometown: South Windsor, CT
● How many years have you been at Trinity-Pawling? Two years
● Interests/Hobbies: Playing hockey, golf, spike ball on the quad, running, and working out.
● What is on your senior year bucket list? Maintain great grades and finish strong, win a New England championship for hockey, and make at least 10 new friends.
● What is your favorite meal in Scully Dining Hall? Steak and lobster spring dinner.
“Being a Prefect means getting to showcase my leadership and my authenticity here to help others learn to do the absolute best at Trinity-Pawling, and also to help maintain a great culture and community.”
Dominic Zani, Prefect of Academics
● Hometown: New Fairfield, CT
● How many years have you been at Trinity-Pawling? Six years
● Interests/Hobbies: Soccer, running, golf, and playing lawn games.
● What is on your senior year bucket list? Catch a catfish in the pond, stay as late as possible every night, and compete in a sport I usually don’t play.
● What is your secret talent? I was number one in the U.S. for Subway Surfers multiple times.
“To me, being a Prefect is always setting the example and guiding the underclassmen in the right direction.”
Jameson Foglesong, Prefect of Victuals
● Hometown: Winter Park, FL
● How many years have you been at Trinity-Pawling? Three years
● Interests/Hobbies: For hobbies, wake surfing and boating are big at home, along with pickleball, very competitive CFB26 tournaments, and lacrosse. As for interests, I’d say political history and college football are some of my larger interests.
● What is on your senior year bucket list? Winning spoons, winning a Founders League lacrosse championship, dominating Dorm Olympics, and winning the cleanest double with my roommate, Mike Savage.
● What is your favorite meal in Scully Dining Hall? Sloppy Joe tater tot casserole and ice cream days, especially when they bring out the caramel sauce.
“To me, being a Prefect means setting an example for not only those around you but for yourself as well, as you are required to hold yourself to a higher standard, as well as working in unison with both the faculty and student body to get different things done and try to make the year as great as it can be.”
Everett Hand, Prefect of Zeal
● Hometown: Harwich, MA
● How many years have you been at Trinity-Pawling? Two years
● Interests/Hobbies: Lacrosse, music, pottery, and grilling.
● What is on your senior year bucket list? Founders League playoffs.
● What is your secret talent? I can remember sports statistics extremely well.
“Being a Prefect is a great honor, and I’m very excited to get to work with the rest of our class.”
Carl Luo, Prefect of the Arts
● Hometown: Guangdong, China
● How many years have you been at Trinity-Pawling? Two years
● Interests/Hobbies: Saxophone, tennis, and squash.
● What is on your senior year bucket list? Crush my college apps early, give a Chapel Talk, and win a Dorm Olympics one last time.
● What is your secret talent? I can whistle.
“Being a Prefect means leading by example, supporting others, and always staying true to myself.”
Trinity-Pawling School is proud to honor Paul B. Rachman ’78 as the 2025 inductee into the Arts Hall of Fame. A trailblazer in independent film and music video direction, Rachman has left an indelible mark on visual storytelling, fusing underground culture with cinematic innovation.
From his early days capturing the raw energy of Boston’s punk scene on a Super 8 camera to directing music videos for iconic artists such as Alice in Chains, Joan Jett, The Replacements, and Pantera, Rachman has consistently pushed creative boundaries. His breakthrough documentary, American Hardcore, which premiered at Sundance and was released by Sony Pictures Classics, is widely regarded as the definitive chronicle of the hardcore punk movement from 1978 to 1986.
Rachman’s passion for storytelling was nurtured during his Trinity-Pawling years, where he developed the discipline and focus that would later define his career. While studying International Relations in college, he pursued filmmaking with relentless dedication, attending NYU Film School during summers and working in television and film production. In 1995, his independent spirit led him to co-found the Slamdance Film Festival, an artist-run alternative to Sundance that champions emerging and independent filmmakers. He continues to serve as a driving force behind the festival, now celebrating its 30th anniversary.
In 2024, Rachman’s documentary Daughters, chronicling young women growing up with incarcerated fathers, premiered at Sundance to critical acclaim. Throughout his career, he has remained deeply connected to Trinity-Pawling, mentoring students through the Senior Independent Project Program and participating in numerous alumni events.
Join us in celebrating Paul Rachman’s extraordinary creativity and enduring contributions to the arts on Saturday, October 4, 2025, from 1:15 – 2:45 PM at Gardiner Theater. Tickets include all reunion activities for the day. RSVP at www.trinitypawling.org/reunion
Join us on Saturday, October 4, 2025, as Trinity-Pawling proudly celebrates two exceptional members of our alumni community: Sam Hemingway ’70 and Tom Hess ’70. Both will be recognized with the Distinguished Alumni Award, the School’s highest honor, for their outstanding lifetime of service to Trinity-Pawling and their significant professional achievements.
The celebration will take place from 9:30–10:45 AM in Gardiner Theater and will serve as a highlight of this year’s Reunion Weekend. Friends, classmates, and members of the Trinity-Pawling family are invited to gather in recognition of Sam and Tom’s remarkable contributions — not only to their professions, but also to the enduring spirit of our School. Their careers exemplify the values of leadership, perseverance, and service that define a Trinity-Pawling education.
This special event is open to all reunion guests, and your ticket cost includes admission to the entire day of Reunion activities. From reconnecting with classmates to celebrating these distinguished honorees, the day promises to be filled with inspiration, gratitude, and Pride.
We hope you will join us as we honor Sam Hemingway and Tom Hess for their decades of dedication and their shining example to generations of Trinity-Pawling students and alumni.
Reserve your place by visiting trinitypawling.org/reunion
Trinity-Pawling School proudly invites the community to join us in honoring the exceptional achievements of our former student-athletes and coaches at the 2025 Athletic Hall of Fame Induction. This celebration recognizes those who have brought distinction to the School through outstanding athletic performance and exemplary contributions both on and off the field.
The event will take place on Saturday, October 4, 2025, from 1:15 to 2:45 PM in Gardiner Theater. Guests are encouraged to RSVP and register at www.trinitypawling.org/reunion. Ticket cost includes access to all reunion activities throughout the day, offering a full afternoon of camaraderie, reflection, and celebration of the Trinity-Pawling spirit.
This year, we are proud to honor the 1964 Varsity Baseball Team, whose dedication and teamwork left a lasting legacy, and the 1990 Varsity Hockey Team, recognized for their skill, perseverance, and impact on the School’s hockey tradition. In addition, individual excellence will be celebrated with the induction of John Hutchinson, whose achievements and commitment exemplify the values of Trinity-Pawling athletics.
The Athletic Hall of Fame serves as a reminder of the enduring influence of our alumni and the powerful role athletics play in shaping character, leadership, and lifelong bonds. We invite all members of the Trinity-Pawling community to come together to celebrate these remarkable athletes and coaches who have reflected honor upon our School.
The 2025 football season looks a little different for Trinity-Pawling. The NEPSAC (New England Preparatory School Athletic Council) moved to a new classification structure, inheriting three classes (A, B, and C). Many teams in New England have been realigned, and traditional leagues like the Founders League have been disbanded for the purposes of football, and schools have been placed into classes and groups that best fit their competitive nature.
In this new look, Trinity-Pawling has joined NEPSAC Class B, competing against many former ISL teams and some familiar opponents like Hotchkiss and Canterbury. During this realignment of New England football, Trinity-Pawling voted against this change and the new-looking schedule. Unfortunately, Trinity-Pawling was in the minority and was outvoted to move forward with the restructuring and realignment. With that being said, the Pride are excited to embark on another football season and get back to the gridiron.
A New Look at Saturday’s:
Buckingham Browne & Nichols (BB&N) (9/19)
Saint Paul’s School (9/27)
Canterbury School (10/4)
Tabor Academy (10/11)
Hotchkiss School (10/18)
St. Sebastian’s (10/25)
Milton Academy (11/1)
Belmont Hill (11/8)
“This new schedule provides our football program with fresh competition and fresh opportunity. It’s a stage where our players can be tested week after week against strong opponents — and a chance to raise the standard for Trinity-Pawling football,” says Athletic Director Chris Gillman ’05.
Looking Ahead:
Head Coach, Rob Davenport adds, “It’s an exciting opportunity for our players to compete at a high level, build new rivalries, and showcase the hard work they put in year-round.” Trinity-Pawling is ready to build new rivalries against high-end competition. Davenport concludes, “Our boys are ready to embrace the challenge and represent Trinity-Pawling with pride.”
Roll Pride!
It’s been an exciting few weeks for the Pride across all sports!
Mountain Biking traveled to South Kent and secured 2nd place overall in both races. Standout performances came from Zack Michalek ’27 and Anderson Pflaum ’27, who both finished first for the Pride in their respective races.
Soccer has seen strong results at all levels. Varsity soccer edged out St. Luke’s 6-5 in a thrilling home match and followed up with a big win at Kingswood Oxford. Michael Savage ’26 continues to shine, scoring multiple goals over the past two weeks and earning Pride Athlete of the Week honors, joined by Max Cornell ’28 and Arthur Figueiredo ’26 contributing key goals. JV soccer rebounded with a comeback 4-3 win over Millbrook, with Nikos Triantafillou ’27 netting three goals and Max Yuan ’27 adding another. Earlier matches included a 0-0 tie at Avon and a narrow 1-0 loss to Gunnery. The 3rd soccer team tied Indian Mountain and defeated Mizzentop, with contributions from several scorers.
Cross Country has been posting season-best performances at Canterbury and Choate. Tanner Braden ’27 led the team with a 9th-place finish at Choate, earning Pride Athlete of the Week honors. Other top finishers included Kai Wilson ’26, Gavin Hida ’27, Andras Horvath ’28, Ry’Mir Williams ’28, Logan Wu ’29, Kevin Fries ’29, Jack Fries ’27, Cormac Theissen ’27, Ronin Mitchell ’27, and Burleigh Weeman ’27.
Football continues to build strong fundamentals despite a loss to St. Paul’s. Standout contributors include Jarious Hogan ’26, Stephen Jones ’26, Ebo Arthur-Mensah ’29, Jack Kim ’26, and Mikey Prince ’27.
The Pride continues to show grit, teamwork, and remarkable individual performances!
Calling all future members of the Pride! Trinity-Pawling School invites prospective students and their families to campus for our Admissions Open House on Saturday, October 25, 2025, from 9:00 AM to 12:00 PM.
This special event is the perfect opportunity to experience the excitement and brotherhood that define a Trinity-Pawling education. Guests will tour our beautiful 230-acre campus, meet inspiring faculty and coaches, and hear directly from current students about life in the classroom, on the playing fields, and in the dorms. From dynamic academic programs to vibrant athletics and arts, you’ll discover how Trinity-Pawling prepares boys to thrive in college and beyond.
Throughout the morning, visitors will learn about the School’s unique commitment to character, leadership, and innovation. Whether you’re drawn to our experiential academics, extensive co-curricular offerings, or the supportive residential community, the Open House will provide an inside look at what makes Trinity-Pawling exceptional.
Registration is required to attend this event. Don’t miss your chance to explore our campus, connect with members of the Pride, and see firsthand how Trinity-Pawling empowers boys to become confident, compassionate young men.
Admissions Open House
Saturday, October 25, 2025
9:00 AM – 12:00 PM
Trinity-Pawling School
700 Route 22, Pawling, NY
Visit our website to register and take the first step toward joining the Pride!
This year, Trinity-Pawling is thrilled to welcome a talented group of new faculty and staff who bring energy, expertise, and fresh perspectives to campus. Among them are Phinn Adams ’18, returning as an Art Teacher, and Sean Heppes, who joins the Mathematics Department.
Phinn Adams ’18 — Art Teacher
After graduating from Trinity-Pawling in 2018 and earning his degree at Hobart and William Smith Colleges, Phinn has returned to campus to teach in the arts. With experience teaching drawing, 3D design, and art history at Lowell Academy, Phinn also brings his skills as an artist, filmmaker, and musician to the Gardiner Arts Center.
What excites you most about returning to Trinity-Pawling?
Seeing the school from the other side of the desk excites me. Trinity-Pawling and its faculty have helped me more than I could express, and I am grateful to be given the opportunity to support current students in similar ways.
What do you enjoy outside the classroom?
Drawing and painting, playing soccer with friends, and making music.
Fun fact about you?
I have a certification in ornithology from Cornell University.
Sean Heppes — Mathematics Teacher
A recent graduate of Mount Saint Mary College, Sean is excited to start his full-time teaching career at Trinity-Pawling. Alongside teaching math, he will also coach basketball and bring his love of cooking and sports to the community.
What excites you most about coming to Trinity-Pawling?
The community, the opportunity to teach math, and to coach basketball.
What do you enjoy outside the classroom?
Basketball, cooking, and fishing.
Fun fact about you?
I once played against NBA player Kyle Filipowski in 4th Grade CYO — and won.
Trinity-Pawling is proud to launch the 2025–2026 Pride Perspectives webinar series this October — a dynamic platform designed to keep our community informed and connected to the School’s core mission of educating and empowering boys. Building on strong engagement from past years, this season will take a deeper look at the state of boys’ education, positioning Trinity-Pawling as a leading voice on the challenges and opportunities facing young men today.
The first webinar, “Boys, Boarding School, and the Loneliness Epidemic,” will take place on Monday, October 20, at 7:00 PM. Head of School Bill Taylor will lead a thought-provoking conversation with Trinity-Pawling faculty, exploring the growing crisis of isolation among boys and how a boarding school environment can be a powerful antidote. Together, they will discuss how Trinity-Pawling’s expertise in boys’ education, culture of mentorship, and close-knit community help students move beyond loneliness to build meaningful friendships, confidence, and a true sense of belonging.
Parents, alumni, and friends of the School are invited to join this timely discussion and discover how Trinity-Pawling’s programs foster connection and resilience in boys. Whether you are a current family or simply curious about the boarding school experience, this webinar offers valuable insight into how Trinity-Pawling prepares young men for lives of purpose and leadership.
Register on Zoom to be part of this important conversation — and help us kick off another exciting year of Pride Perspectives!
It’s fall on campus, and the energy is palpable. The boys are tackling new classes with curiosity, standing together at athletic competitions, gathering as a community in Chapel, and finding their voices through the arts. Behind each of these moments are mentors who believe in our boys — guiding, challenging, and inspiring them to grow.
Through the Trinity-Pawling Fund, this transformative experience comes to life. Your support provides the tools in the classrooms, the gear on the fields, and the experiences that help boys discover their distinctive gifts and talents. It ensures every boy is supported in his journey to develop critical thinking, effective communication, ethical citizenship, thoughtful collaboration, and self-awareness — the hallmarks of a Trinity-Pawling graduate.
Did you know? Gifts to the Trinity-Pawling Fund support initiatives that have immediate, tangible impact: from new classroom technology and co-curricular equipment to faculty mentorship and professional development. Your generosity is visible in every corner of campus, every day.
Ways to give:
Online: www.trinitypawling.org/give
Venmo: @TrinityPawlingSchool
Phone: 845-855-4836