In its second year running, the Winter Projects allow students to select from a broad range of interdisciplinary course offerings and pair up with two teachers (one from each discipline) on a project that requires using the tools from both disciplines. As one of the three prongs of the Practicum for Civic Leadership, these projects aim to teach students critical 21st century skills such as working collaboratively to understand an issue, learning how to give an oral presentation both as part of a group and as an individual, as well as learning how to ask the right questions when confronted with a challenge.

Our spotlight project this month is the Key Club Campus Tour in Mandarin.

The goal of this project was to create a video tour of the School entirely in Mandarin for the purpose of being used as an admissions tool for prospective students from China who may be unable to experience a tour on campus. Kenny McDougal ‘17, one of the 3 seniors working on the project, says, “We all enjoyed being on set. As the ‘actor’ it was Jack Makris and Hunter Olstein’s job to direct me to be relaxed and have fun.” McDougal adds, “The biggest challenge for me was memorizing the script (Chinese is really hard!).” The students are proud of their finished product and hope it will help the admissions office in the future.

“Watching Kenny develop the narrative, work on pronunciation and on tones, and consider the challenges of translating a live tour to a professional video with high production values was a learning and an enlightening process for me as well,” says Mandarin teacher Mark Corliss. “He nuanced well all aspects of the project.  In conjunction with Hunter Olstein, videographer; Jack Makris, key grip; and Leo Chen, editor, Kenny’s work showed that when given time and space, students are able to accomplish much.  I am very proud of the work by the members of this project,” Corliss concludes.

Watch the campus tour here.

For a full list of Winter Projects, view the course catalog.


Dylan Penebre ’01 and Ty Macomber ’02

You’re sitting at the bar of your favorite establishment while the server punches your order into the computer, or the host scans a screen for available seating. Chances are the software running that program was developed by Dylan Penebre ’01 and marketed by Ty Macomber ’02.

In 2011, these two high-energy alums joined forces in Boston to create PointOS, a tech company that provides point of sales and payment solutions for restaurants, bars, and nightclubs. The system handles day-to-day operations for a business, such as tracking orders, assessing inventory, and managing the time clock for employees.

“Restaurateurs need point of sales systems at an affordable price,” Penebre explained. “Our ability to provide that service put us on the map.” That map now includes more than 10,000 customers across the U.S. and a presence in 33 countries around the globe. “We design the software that automates the ordering process for servers and provides the analytics to track data of sales and inventory.”

Penebre and Macomber connected at T-P through varsity football and baseball. Although a day student senior year, Penebre became the fourth roommate in the Barstow triple Macomber shared with Brendan Billone and Joey McElligott. When Penebre moved to Boston in 2007, the first person he called was Macomber. “I needed him to help move the couch into my apartment, and we reconnected from there on.”

In 2010, Penebre and another business partner developed the software concept that laid the groundwork for PointOS. The company started in Penebre’s basement in Newton, MA, and Penebre was recruiting his former teammate before Macomber even knew it. “I knew he would be the salesman we needed to make this company a success,” Penebre said. “My first desk was a pop-up poker table,” joked Macomber.

Both men readily acknowledge that Trinity-Pawling shaped their lives and that the School’s philosophy is woven into the fabric of PointOS. “We even use aspects of the effort system to motivate and reward our employees,” admitted Penebre. Moreover, both believe Trinity-Pawling’s competitive athletics program fuels entrepreneurial hunger. “Starting a company is hard, sales is hard,” said Macomber. “However, T-P taught us that persistent effort yields results.”

“Coming to Trinity-Pawling from a small public school gave me a chance to compete in a wider playing field,” Penebre said. “I met successful alumni who came back to campus and opened my eyes to a greater range of opportunities.” Macomber added, “The effort system trained me to work hard and be ready to learn new things. In software and sales, I always have to be on my toes to stay ahead of the curve.

And the brotherhood? “We fostered a bond at Trinity-Pawling,” Penebre said. “When it gets tough, we rely on each other.” Seems like a solid business philosophy.

The Visionary and the Marketer

Nick LaFontaine on “Rebuilding Richmond”

One of the highlights of the winter term and of Bill Taylor’s inaugural year as Headmaster at Trinity-Pawling has been his project-based learning initiative.  The faculty was challenged to create interdisciplinary projects with other teachers to spark the interest and the imaginations of our budding young scholars.  In “Rebuilding Richmond,” Kevin Richards and myself tasked the boys to rebuild part of the city of Richmond post-Civil War, either during reconstruction or modern times, through the lens of an urban planner.

We required the boys to research and write about the destruction of the capital of the confederacy, Richmond, and specifically the region of city they wished to redesign.  The boys not only had to become familiar with the historical, political, and economic sensitivity of rebuilding an area of the city, but had to do so being conscious of basic issues urban planners must address such as pedestrian safety and traffic flow.  The boys were required to attend meetings to work on their projects and were given a series of checkpoint assignments throughout the winter term to keep them on task, including reading two brief primary sources about the city and the destruction of the city, creating a Google map of Richmond, referencing their sources with a works cited page, highlighting a geographic area of the city, creating a rough draft of how they proposed to rebuild that area, and finally present their rebuilt geographic area of Richmond including certain geometric features.

One shining example was Min Sang Ki’s “Rebuilding Richmond” project. In fact, other teachers who have since seen Min’s design have been thoroughly impressed as well. Min was active throughout the project working intensely from start to finish.  It paid off!  Min decided to physically construct, to scale, the “State Capitol Building” and “Mayo Bridge” areas leading into Richmond during the time between Reconstruction and contemporary times.  He accompanied his model with a detailed PowerPoint presentation that highlighted aspects of his project, including the required geometric features.  Min’s construction of the concrete truss style Mayo Bridge, including a description of the reason why the pieces of the bridge were slightly separated, and the tobacco field created underneath the bridge showed how much thought and care went into the project.  As you followed the bridge into town, it led you to a stone Market Street complete with three businesses including Min Tea, Antique Shop, and Meat Store.  He designed the rebuilt Capitol Building after the likeness from the District of Columbia including Roman columns.  Min also included telegraph lines along with all the required geometric features.  Brilliant!

– Nick LaFontaine

Faculty reflection on Winter Project

“This is Bill Taylor here on WKCO.”

The “Bill and Pete Show” aired for only one year, but it secured Bill Taylor the gig as host of a weekly radio show at his college radio station, WKCO, for all four years of college.

In those days, the kids who ran college radio shows were the real music fans. “Music was all vinyl and, therefore, you used two different turntables,” recalled Taylor, “so I had fun with the challenge and art of mixing the end of one song into the beginning of the next one.” Taylor didn’t study radio production, or have any special training, he learned “by doing it.”

College radio became an integral part of Taylor’s life at Kenyon College. Inspired by disc jockies Scott Muni of WNEW in NYC and Larry the Duck on WLIR, “Bill’s Radio Show” featured the “new wave” music of the early 80’s. Taylor was fortunate to have popular night time slots for featuring his favorite bands like Talking Heads, U2, New Order, The Clash, Depeche Mode, The Cure, The English Beat, and The Jam, to name a few. By senior year, Taylor’s radio show was the pre-dance party radio show that everyone listened to on Saturday nights. Taylor was voted Best Radio Personality during his senior year – 1985. “That was a highlight!” he recalled.

“Hosting a radio show made me much more comfortable speaking in public because of the semi-anonymity that is provided by the radio,” said Taylor. “I learned how to speak succinctly and with a focus on clarity.” “Now there are many people who I am sure would like me to speak less!” he joked.

This winter, Taylor co-guided a self-designed Winter Project by juniors Ryan Winn and Chris R. Taylor, who pursued a research project that combined their passion for music with the history of local broadcast radio. Their project culminated with their own hour radio show at the local Pawling Public Radio, complete with a Bill Taylor cameo. “It is important that students learn to follow their own interests and passions, in addition to following a prescribed course of study,” he said. “Both are essential.”

Chris and Ryan’s archived show can be heard on

The value of following passions

Jonathan Kalin ’10

Jonathan Kalin ’10 returned to campus in March to give a presentation in Gardiner Theater to Trinity-Pawling students about “Party with Consent”, the sexual violence awareness movement he started at Colby College in 2012.

The organization strives to promote awareness about consent in attempt to prevent sexual violence through education. Kalin’s movement has a presence on more than 30 campuses nationwide, and he’s become a well-known spokesman for ending sexual assaults on college campuses. “It’s about trying to actively change college campus culture from within,” Kalin says.

In his address to students, Kalin emphasized the power of speaking out, and encouraged students to do so in situations when they felt unsure about whether or not they should. He seeks to include men in the conversation about issues surrounding sexual violence, particularly on college campuses, and he charged the boys with the notion that they, as future college students, have the power to change campus culture.

“Because of my lived experience as a man, I am really excited about the work within all male communities.” Kalin says. “When I was at Trinity-Pawling, I had the lead in the school play, which was something I had always wanted to do. I was also a captain on the basketball team, kind of like Zac Efron in High School Musical,” he laughs. Admittedly though, Kalin wasn’t as confident as Zac Efron’s character in the film. “I definitely benefitted from that narrative, thinking, ‘that guy is so cool that he can be who is he is, and that makes him more of a man.’ But for me it was a little scary. I didn’t want the guys on the team to know I was in the play. Of course, the coach told the team to go see me in the play and give their support. I learned solid values here, and it definitely got me to start thinking more about these issues.” Kalin explains.

Kalin was recently featured in The New York Times Magazine. Read the full article here.

Raising awareness one campus at a time

Economics of Hockey

The Economics of Hockey project, led by Michele Carlin and Scott Harff, explored a hypothetical scenario in which students had to decide if building a new Hockey rink would be feasible or if refurbishing the current rink was a better option.

“As would most young athletes, the boys approached the project with the unstated intent to prove the need for a shiny new facility,” explains Carlin. “Until they learned how to create a spreadsheet and utilize its functionality with Algebraic formulas, the data told them little information. After the reality of the calculations set in, they set to work with interview questions for our outside participants.” Surprisingly enough, the boys found that their interview answers gave them pertinent information about how to move forward in their decision for the rink. Harff adds, “One group decided not to build a second hockey rink following an interview citing that the families who are interested in summer hockey had preconceived opinions about an established program in Danbury, Connecticut and would continue attending that program.”

Scott Harff, Economics teacher, lifelong hockey player, and coach, brought a unique viewpoint to the project. He wanted students to gain an understanding for how many fixed and variable costs go into the running of a hypothetical rink. Since the bulk of the hypothetical rink’s ice time is used by a school (as is the situation at Trinity-Pawling), Mr. Harff also wanted the boys to gain an understanding of the amount of foregone income associated with a rink run on a campus. Bearing that in mind, students created formulas that would pull together all the pertinent data and provide a bottom line, decision making tool.

Overall, the project was a success. “It was enlightening on both sides of the desk,” recalls Carlin. “To work with such a cross-section of ages and academic experiences truly challenged us to create an atmosphere that would provide relevance to all involved. To watch the boys support each other during the project and the presentation was the best reward of all. They brought out the best in each other.”

Winter Project spotlight


“It’s a beautiful thing,” is how Slade Mead describes Early Decision.  “It’s rather tricky,” explains Mead, the Director of College Placement, “because you need to make sure first, that school is absolutely your first choice; second, the college in question has Early Decision; and third, most students’ number one school is a reach; therefore, the acceptance rate is still brutal.”  Early Decision is a process where an applicant applies in the fall and gets a binding offer of admission before the new year. This year roughly 25% of the class applied to and was accepted into their first choice schools.

“To those seniors who did apply Early Decision and got in, I offer my congratulations. To those who applied ED and either were denied or wait listed, I applaud you for your effort and taking a risk.” Mead then gets somewhat philosophical, “Hey, I love kids finding a first choice school and shooting for the stars.  If it does not work out for someone, at least he grew from the experience.” Mead explains, “The classes’ average could have been even higher, but many students picked top schools that do not offer ED. That is why if a rising senior finds the perfect school that offers ED and he gets accepted, it’s a beautiful thing!”

Here’s the current Early Decision list for the Class of 2016:

Student College
Brandon Bank Furman University
William Michael  Berghold Kenyon College
Caelahn Bullen Cornell University
Oleg Gentry Hartwick College
Aidan Gorman University of Richmond
Daniel Hoag Rensselaer Polytechnic Institute
Zhifei Li Occidental College
John Litscher Skidmore College
Eric Mawdsley Sacred Heart University
Connor McClelland Marquette University
Kyu Yeol Paik Carnegie Mellon University
Paul Rasimowicz Cornell University
Fitzhugh Fitz Reese Tufts University
Henry Rickert Elon University
Michael Schek Rochester Institute of Technology
Justin Scott Hobart and William Smith Colleges
Ryan Seibold University of Richmond
Tyler A. Trammell Hobart and William Smith Colleges
Bayley Tranmer Hobart and William Smith Colleges
Robert Walker Wofford College
Andrew Wyman St. Lawrence University
Congratulations boys!

Allison Whipple Rockefeller ’76

Allison Whipple Rockefeller ’76, a Putnam County native, joined Trinity-Pawling in 1974. A lover of nature, she enjoyed the “uplifting and inspiring” beauty of campus. During her three years at T-P, Allison developed lasting relationships with faculty members who ingrained in her a strong value system and direction that she’s carried throughout her life. When reflecting on her time at Trinity-Pawling, Allison shared that the support and dedication from faculty members Bill Smythe and John Lloyd Owen made a profound impact on her life, stating: “The irony is, we think we don’t need structure when we are teenagers, but that is what we crave most. It is the single greatest gift that Trinity-Pawling gives us forever. It is the foundation of the life I live today, one of discipline and expectation for myself.”

Allison embodies the mission of Trinity-Pawling and lives a life of fides et virtus. She has dedicated her life to supporting national, regional, and community-level conservation causes – focusing on parks and open spaces – and to championing women who support environmental initiatives. Allison served as the first alumna Board Chair of the Student Conservation Association – an organization she volunteered with during her time as a student at Trinity-Pawling. Allison has also served as a Commission Member for the New York State Department of Parks, Recreation, and Historic Preservation under four governors and is a longtime Board Member of the Central Park Conservancy’s Women Committee. She is the founder of Cornerstone Parks, the Pumps-to-Parks Initiative designed to create a network of small parks and community centers from the more than 150,000 abandoned gas stations in towns across the United States. Allison is also the founder of National Audubon’s “Women In Conservation” and started, in 2004, it’s prestigious Rachel Carson Award, one of the most important national awards for American women leaders in the environment.

Thank you, Allison, for your commitment to nature and for serving as an example to the entire Trinity-Pawling community of how to live a life of faith and virtue!


Lifelong conservationist and inspirational member of the PRIDE

Student Spotlight: Kyle Miller ’18

Kyle Miller ’18 is as passionate about the written word as he is about ice hockey. The sophomore hockey recruit from Bristol, CT, speaks of hockey as “a great game that requires smarts and toughness.” Head Varsity Hockey Coach Robert Ferraris ’93 describes Kyle as having “strong fundamentals and game intuitiveness; he is rugged and fearless without sacrificing the good of the team.”

It was Kyle’s fearlessness on the page that prompted instructor Tim Pillsbury, the faculty advisor for Trinity-Pawling’s student newspaper The Phoenix, to take note of Kyle’s passion for writing and personal expression. “I was drawn to the rawness and emotionalism of his work, as well as his courage.” Pillsbury suggested that Kyle pursue an independent project-based learning assignment during the winter term.

Kyle ultimately published a 65-page book titled Black Eyes Open. Curating and editing dozens of poems that illustrate a journey from darkness to light, he produced a prolific and intimate body of work that is “rare to see in someone of any age, let alone a high-school sophomore,” adds Pillsbury.

Because the project was required to be interdisciplinary, Kyle built upon his foundation of self-expression through writing with an investigation into photographic self-portraiture. He opted to go beyond “the selfie” and examined self-portraits created by the masters. “Kyle bravely embraced the poetic photographic process,” said Connie Rafferty, the digital media producer with whom he worked to create the photographs. “His vision for the portraits very quickly moved beyond the literal to the metaphorical. And the final result is powerful.”

Miller produced the book while maintaining his normal course load of advanced placement courses and being an outstanding contributor to the Trinity-Pawling Varsity Hockey program this winter. Coach Ferraris adds, “Kyle is reliable on both sides of the puck, and is a rare defensemen for his age. We are lucky to have him.” Nurturing his love of poetry was, of course, a goal for Pillsbury, “When someone loves something as unique and valuable as poetry that needs to be fostered.” And Kyle is pretty happy with the result, “I am grateful for this opportunity and the support I received throughout this process. I hope this collection will help anyone navigate hard times and move towards the light.”

Miller shoots…and he scores!

Fearless on the ice and on the page


The Pride is back from their three-week vacation, and the spring athletic season is now fully underway.

Over the break the lacrosse team traveled down to Philadelphia to scrimmage three teams from the tri-state area. The Pride faced off against the Episcopal Churchmen, the Chestnut Hill Blue Devils, and the Tower Hill Hillers from Delaware.

Forty members of the team then traveled down the east coast to Orlando, Florida to practice in the warm temperatures and scrimmage the University of Tampa, a Division-2 college team.

Head coach, Nic Bell commented, “I am really pleased with how our upperclassman lead the way for the younger guys and set good examples on both trips. It has been a very positive and productive start for the team, and the trip to Florida was the best spring trip I have had in my five years at Trinity-Pawling.”

The lacrosse team will play their first game of the season this upcoming Saturday against West Point Prep at home beginning at 2:00 pm.

The varsity baseball team also made their way down to Florida to play five scrimmages at the “Florida Coast Spring Training” in Fort Pierce. The young team, with only a few seniors to speak of, was able to hold their own in the practice games and come away with a great deal of runs and solid pitching performances.

Upon returning to Trinity-Pawling, the baseball team played another scrimmage against Hopkins this past Wednesday. With a couple players still not back from vacation, the Pride was able to play competitively with solid performances from juniors Forrest Ruiz and senior pitcher Will Rickert.

The first game for the baseball team will be Monday, April 4th at the Canterbury School.

Golf and Track will not open their respective seasons until Saturday, April 16th, and Tennis will start competition on Wednesday, April 13 at home against Millbrook.

Roll Pride!

Spring sports

Community Service Day

On Sunday May 1, 2016, Trinity-Pawling School will host visitors to campus to celebrate the greater Pawling community. MayDay is a fundraising event to benefit two local charities.

Ryan’s Foundation is a non-profit organization founded with the mission to raise funds to support children living in the Hudson Valley that are afflicted with cancer or other life threatening diseases, by improving the quality of life for them and their family while they fight illness. The Pawling Resource Center provides food, rides to medical appointments, and the grocery store, loans for medical equipment, and many other services to community members at no charge.

Trinity-Pawling, in conjunction with Mizzentop Day School and Pawling Central School, welcome families and friends to the campus for a day of competition and fun. The main event for the day is a 7k “Extreme Cross Country” Race that will pose a challenge for even the most conditioned athletes. Hills (many!), mud, and physical challenges are part of the course that travels throughout the 180 acres of the campus. For those looking for a slightly more relaxed physical activity, there will be a walking course as well.

Students of all ages are encouraged to participate in the walk or the run, and there will also be a kids race (½ mile) on the track for the more competitive youngsters (under 10) in attendance. There will also be a food drive to collect dry goods for the Pawling Resource Center. Details at

Students and youngsters can enjoy inflatable slides, a climbing wall, obstacle courses, sticky walls, twister, jousting, a dunk tank and other interactive games throughout the duration of the afternoon. Lunch is included for registered race / walk participants as well as to the students and children who donate. There will be additional food for purchase from local vendors to compliment what is provided.

Campus opens at 10:00 AM for registration and food drops. The 7k Race will start at 1:00 PM and the May Day event will conclude at 4:00 PM. Registration for the walk, run, and kids events will be done online on the Ryan’s Foundation web site at a discounted rate or can be done on site at Trinity-Pawling School on Sunday, May 1. Pre-registration will be accessible online (and is highly encouraged!) by Monday, April 4.

Please spread the word, register, donate and join us for MayDay at Trinity-Pawling School to help two excellent organizations that make other lives better in our local community!

Join us on May 1, 2016!


When you give, you invest in a brotherhood that lasts a lifetime, an education that turns hope into achievement, and hard work into results.

You make great things possible!

There’s still time. If you haven’t supported Trinity-Pawling this year, the fund closes on June 30, 2016. You can direct your gift to the area of the School that means the most to you. Find your giving options here. Thank you.

Roll Pride!

Help us move forward!


Headmaster Bill Taylor and Jennifer Taylor have enjoyed meeting many of you at receptions during the first half of the year.

The next stop for Bill and Jennifer will be in Pittsburgh on Tuesday, April 12. The reception will be held at the Duquesne Club, from 5:30 – 7:30 PM.

Bill and Jennifer will be hosted by Jen and TJ McCrady ’85.

Come celebrate our momentum and share Trinity-Pawling’s vision for the future. Roll Pride!

For more information visit or contact Beth Bryant: or 845-855-4833

Join us in Pittsburgh!