From Pilgrim Road SPRING ’25

blonde girl in pink dress and girl of color in navy blue dress ring bell on stage

Convocation Lays the Groundwork for a Perfect Year

To mark the beginning of the 139th school year, seniors made their grand entrance into the David E. and Stacey L. Goel Theater to the Mission: Impossible soundtrack. Calling the assembly of students “bright-eyed and cheery,” President of the Winsor Corporation Allison Kaneb Pellegrino ’89, P’21, ’22 spoke about the founding of Winsor and reminded students, “We are all stewards of this school for a time.”

President of COLLECT Nidhi Mallavarapu ’25—dressed as Leonardo Da Vinci’s Mona Lisa—collected wisdom from fellow seniors answering the question, “If you could go back and give yourself advice when you were starting at Winsor, what would it be?” She distilled their responses into 12 pieces of advice ranging from aspirational—“don’t just live in the moment, thrive in the moment”—to practical—“get enough sleep.”

Inspired by the 2001 heist movie Oceans 11 and the 2018 all-female spinoff Oceans 8, Senior Class President Elizabeth Fitzpatrick ’25—dressed as Minions supervillain Vector—introduced the Class of 2025’s senior theme: Oceans 2025. Putting together the perfect crew is key

to any heist, and Elizabeth described fellow senior classmates—“a cunning, skillful, driven group of people”—as the perfect crew to “team up for one last year and for one last mission.”

Head of School Sarah Pelmas used the Summer Olympics to put the school year ahead in context, pointing to many extraordinary moments of women uplifting other women. In one example, Ms. Pelmas dove into the media frenzy surrounding Australian swimmer Ariarne Titmus and American swimmer Katie Ledecky, who were considered rivals by commentators, but in reality count each other as inspirations. As Ledecky took gold in the 800-meter freestyle event to become the most decorated female swimmer and most decorated American female athlete in history, Titmus captured a silver in the next lane over. And yet it was Titmus who raised Ledecky’s arm aloft in celebration, and offered her a hug and congratulations.

With their mutual admiration as inspiration, Ms. Pelmas challenged everyone to set a new (school) year resolution to “be like all those amazing women athletes, who work as hard as they can, who hold one another up, in good times and bad, who are proud of each other, and who comfort each other.”

Ms. Pelmas offered suggestions for what this could look like in practice: “We can start with something easy: start by noticing the people around you and what they are up to. Be proud of them, build them up, give them positive feedback. Challenge yourself to offer words of honest and wholehearted support every day. When you do this, you will find that you are working squarely in the tradition of this school—where we speak our minds and also work to build and grow a healthy, forward-thinking community.”

The gentle tinkle of Miss Winsor’s bell opens and closes each school year, a tradition dating back to 1910. Class IV Council Heads Ani Andersen ’29 and Isha Vachhani ’29 did the honors and told students earlier in the program, “Winsor is a perfect place to try new things.”

Quadrennial Community Curriculum Day Returns to Campus

Every four years, timed to the presidential election, Winsor’s on-campus community shifts from regularly scheduled activities and comes together for Community Curriculum Day.

During the day-long program on October 29, 2024, students, faculty, and staff participated in two all-school assemblies, attended workshops of their choosing, and debated whether or not to implement a new division-specific initiative.

To start the morning, Winsor’s Upper School met in the Brock-Wilson Gymnasium to hear arguments for and against the proposed Upper School ballot initiative: Should we have a monthly no-cell phone day? While 41% of the Upper School student body wanted to forgo cell phones once a month, ultimately 59% of students who cast votes wanted to keep their phone access. The initiative did not pass.

Lower School students had their own ballot initiative: Should the Lower School have a monthly “Mix It Up Lunch” day? The proposed initiative would authorize the Lower School Council to plan monthly lunches where students would be placed in mixed-grade level groups to engage in planned activities. While the initiative did not pass, students still enjoyed exercising their right to vote at the polls.

Complete with privacy barriers and volunteer poll workers, students in both divisions were invited to cast their ballots and even came away with “I voted” stickers. Had either initiative passed, Winsor’s administration was prepared to honor the students’ wishes.

“It was important to us to simulate an authentic voting experience for the students,” explained Math Faculty Jessica Wang. “We wanted to demonstrate that election outcomes have real consequences.” In addition to her teaching role, Ms. Wang is the Upper School community and inclusion coordinator and was instrumental in developing the voting experience for students.

The two assemblies gave members of the community time to gather and reflect on important issues of the day. The first, America in One Room with Alice Siu, associate director of the Deliberative Democracy Lab at Stanford’s Center on Democracy, Development and the Rule of Law, examined how the widespread and booming use of streaming platforms and social media has created a society without a collective understanding or common experience. The second, All Politics Is Local, was moderated by Winsor alumnae Anshi Moreno Jimenez ’15, who works in policy and strategic planning in Boston Mayor Michelle Wu’s office. Anshi was joined by a panel featuring Massachusetts State Representative Chynah Tyler and Director of Communications and Community Outreach Hodan Hashi, who works in the Office of City Council President Ruthzee Louijeune. The rousing discussion covered a variety of topics, from imposter syndrome to low participation and voter turnout in Boston elections.

Students were at the center of the day, not only participating in assemblies and workshops, but leading them too. Lara do Rosario ’26 and Liana Min ’26 led “Religion in the Election.” Their workshop looked at how the politics of religion might affect the 2024 presidential election. “Creating the agenda for the workshop was pretty difficult because it required us to find the right balance between discussion and activity. Since we didn’t know how talkative our participants were going to be, we weren’t sure how the turn-and-talk activities would go,” explained Lara. “I felt in the end, our agenda was very engaging and mixed because we did a myriad of activities, including a ‘match the quote with the speaker,’ reacting to a propaganda video, and countering common assumptions about the candidates’ religious backgrounds.”

Ultimately Lara’s workshop worries were for naught because student participants rose to the occasion. “I was surprised at how much people had to say,” she said. “People were confident and open in discussions.”

Upper School students planned and conducted more than a dozen workshops on Community Curriculum Day based on their own interests and of their own design. Angie Fang ’26 and Demira Parekh ’26 led “Mind the Gap: The Psychology Behind Civic Engagement.” The interactive workshop looked at the mental processes behind civic engagement, the divides that often keep people apart, and what we can do to bridge those gaps. “I realized that a lot of people knew about the psychological processes behind aggression and group dynamics but just didn’t know what they were called,” said Angie. “Once we put a name to something, everyone was like, ‘wait, that makes a lot of sense.’”

Workshop design and facilitation doesn’t just help students develop leadership skills, it also allows them to think critically about why they’re attending workshops and what they hope to get out of the experience. Lara shared, “Being a [workshop] leader taught me how to be a good participant in workshops. …I’m glad I got to lead one here at Winsor.”

At the Martin Luther King Jr. assembly, Lower School students Sydney Hall ’30 and Aarna Sundaram ’29 reflected on their participation in the Community Curriculum Day workshop “Letters for Global Change.” The goal was for each student to write a letter to a local elected representative explaining a global issue they want to see prioritized. Sydney chose to write about immigrants in Boston and the challenges they often face in finding housing and jobs when they arrive, while Aarna wrote about environmental justice and the economic inequities that disproportionately affect different areas. Drawing on Dr. King’s fight for marginalized people and advocacy for equality, they explained, “The [workshop] session allowed us both to practice global citizenship, civic action, and persuasive writing. As we reflect on Dr. Martin Luther King Jr.’s birthday this year, each of us can use these skills to help bring us closer to the just society Dr. King envisioned.”

While Upper School students led most of the day’s workshops, English Faculty Lisa Stringfellow, who is Ms. Wang’s counterpart as Lower School diversity and inclusion coordinator, noted that the Lower School Planet Protectors club helped plan “Climate Politics” in conjunction with Winsor alumna Jess Nahigian ’10, the state political director of the Massachusetts chapter of the Sierra Club. Together they looked at the role environment plays in elections, what students can do to help despite being too young to vote, enjoyed a planet craft project, and played a climate game.

In addition to Jess, several other alumnae returned to campus to run workshops, including: Sage Stossel ’89 (“Political Cartooning”), Marisa Greenwald Keeney ’02 (“Health Care in America”), Leila Sales ’02 (“How to Change Your Community”), and Hailey Fuchs ’16 (“Covering Presidential Elections”). Winsor parent Jeannie Suk Gersen P’25 participated, too (“The Supreme Court and the 2024 Election”).

“It was fun to be back at Winsor,” said Sage. “I was impressed to see how game and fearless the students were about trying their hands at their own cartoon-style drawings.

I hope they had fun, and that some of them might continue to experiment with cartooning as a tool for sharing their perspectives.”

Leila found the experience rewarding too. “The students were thoughtful, communicative, independent thinkers with big ideas for how to change the world. I loved seeing how their minds worked,” she said.

History Faculty Julian Braxton, who holds the Bezan Chair for Community and Inclusion, was the true mastermind behind Community Curriculum Day. His goal was for students to cultivate lifelong tools that will stay with them beyond the 2024 election. “It’s a challenging dilemma for students when they find out they fundamentally disagree. Ultimately, I hope students learn tools to have different discourse across all aspects of their life,” he said. “I want Community Curriculum Day to be an opportunity to think about and engage with different perspectives and respectfully disagree.”

By all accounts, the quadrennial Community Curriculum Day was a success. “The best part of Community Curriculum Day for me was hearing perspectives I had never encountered when people took risks to present an unspoken opinion,” shared Lara do Rosario, who led the workshop “Religion in the Election,” adding, “I hope that continues.” Angie Fang, who led “Mind the Gap,” agreed. “Even if political opinions are different, Winsor students have shown that we can approach each other with an open mind and engage in civil conversations. There’s a lot of hope for the future.”

group of seven people, girls and parents holding awards

Debaters Earn Coveted "Top School" for the First Time in Winsor History

Colloquially called “Internationals” and “Worlds” by those on the circuit, there are two major speech and debate tournaments held annually—Worlds Speech and Debate competition and the International Independent School Public Speaking Championships (IISPSC). Winsor has been sending a delegation to these two competitions for decades.

Under the leadership of longtime Speech and Debate Advisor Jean Berg, who is celebrating 40 years at Winsor (see page 12), Winsor students have competed over the years in locations such as Argentina, Australia, Botswana, Canada, Cyprus, England, Lithuania, South Africa, and the U.S. Nika Bigelow ’25, Theo Zarrow ’26, and Emily Zhang ’25 represented Winsor’s Speech and Debate Team at IISPSC in Bermuda this past October. Held over four days, the competition featured 100 top speakers from 34 different schools across the world.

Speakers are required to enter three competitions at IISPSC. While all three students competed in Impromptu Speaking and Interpretive Reading, Nika and Emily additionally competed in Persuasive Speaking, while Theo added After Dinner Speaking to her lineup. After three days of powerhouse scoring, Nika, Theo, and Emily each made it to the finals in two of their three events.

Ultimately, Nika finished 14th overall in the speaker ranking. Emily won the Impromptu Speaking competition, tied for third in overall speaker ranking, and also tied for the coveted “Top American Speaker” award. In a stunning finish, Theo won the After Dinner Speaking Competition and finished fifth overall, earning her a berth at the 2025 Worlds Speech and Debate competition this spring in Malaysia.

Because of their tremendous efforts, Winsor took “Top School” at Internationals for the first time in school history.

“They were wonderful to work with,” said Ms. Berg, who worked with each student individually, meeting at least once and sometimes twice a week on Zoom during summer break. “Ned and I are proud of Emily, Nika, and Theo, and elated by the awards and the well-deserved accolades they received at Internationals,” she added. Ms. Berg coaches the team with fellow Debate and Speech Advisor and English Faculty Ned Henningsen. Winsor Speech and Debate was founded in 1895.

Playwright in Her Own Right

Student-directed plays have been a part of the Winsor curriculum for well over a decade. But it wasn’t until recently that a student wrote and then directed their own show.

For years, students have been invited to select and propose a play. As student directors, they manage everything from costume direction to staging. Mina Feldman ’25 took the student-directed play a bold step further and wrote her own. Twice.

Mina made her playwright and directorial debut as a Winsor junior with Course Correction. “The college counselor at this fancy private school is murdered,” explained Mina, who included bits of herself and her own experiences in the play. “This tenth-grade detective takes it upon herself to solve the case. The narrator, who is the detective’s sister, has just been deferred from her dream school, so she’s sort of reeling from that. It’s about solving the mystery but also about how these two sisters can navigate this place where excellence is currency—how they deal with the culture.”

During senior year, Mina was back at it again, and wrote Spelled Out in the fall. Theater Director Jeremy Johnson remembers Mina scouring his bookshelves, reading plays and hunting for the right show to direct, but she couldn’t find one. “She walked into my office and said, ‘So, I wrote another one,’” recalls Mr. Johnson. “I read the play, and I knew we had to make it happen.”

From Mina’s director’s note, Spelled Out explores the “intersection of grief and teenagerdom with supernatural, ghost-story flair.”

The play follows three friends and a tag-along younger brother who venture into the woods at midnight to try and connect with a deceased friend using a grimoire and Ouija board. The younger brother unexpectedly has the gift of possession, and two spirits visit his corporeal form. As the group becomes frustrated that they can’t reach the spirit they want, tensions run high.

Mina shared, “Over the course of our rehearsal process, the cast of Spelled Out and I have come to think of grief and adolescence as parallel processes. Both experiences are marked by irreversible change. Both render you powerless and confused. And both will leave you pissed off and distrustful and emotional at all the wrong times.”

Mina credits Mr. Johnson for developing her love of theater, and for giving her a shot. “He’s a really great kind of mentor,” shared Mina. “The fact that the Performing Arts Department gave me that opportunity is just so cool. It’s beyond anything I could have thought possible.”

As she finishes senior year and looks ahead to what’s next, Mina has her sights set on being a director and playwright, experiences she got to have at Winsor. “Here, you can have an idea, just a hope or a dream, and you can make it happen. I think this is a really special thing that’s really unique to Winsor. You can talk to people and say, ‘I want to do this,’ and you’ll find people who support you, whether that’s your peers or your teachers.”

young girls dressed in red with face paint smiling

Celebrating the 29th Annual Under the Lights

School pride was on display in the fall for Spirit Week where students, faculty, and staff donned their most festive attire in the lead-up to Under the Lights (UTL).

Each year, UTL is organized by Students Advocating School Spirit (SASS). This year’s roster of spirit days included “dynamic duos,” where costumed pairs like pineapple and pizza, Batman and Robin, and Wicked’s Glinda and Elphaba navigated campus together. On “idiom day” outfits explored popular phrases like “raining cats and dogs,” while on “local legends day” students showed their Beantown pride as iterations of Make Way for Ducklings and numerous Dunkin’ tributes.

Spirit Week always culminates in Red Day, when the entire school community enjoys a special schedule that ends in a pep rally held in the Brock-Wilson Gymnasium. For weeks, entire grades met during community time to conceptualize and practice their cheer performance. While every class shone in their routines, the Class of 2025 took home first place on their final Red Day.

Hundreds of current Winsor families and alums returned to Pilgrim Road for games of Winsor athletes on mid, JV, and varsity teams across field hockey, soccer, and volleyball. The Winsor Parents’ Association amped up the atmosphere with decorations and a spirit table stocked with sunglasses, foam fingers, face painting, and a photobooth. Onlookers watched games and noshed on pretzels, hot dogs, and chili.

To close out the weekend, on Sunday, October 20, Winsor pride continued with three boats racing in the 59th Head of the Charles Regatta. For the first time, 19 athletes competed for Winsor. They walked away with fantastic results managing to requalify two boats for next year, and had a blast on the dock with amazing support from families, friends, and alums.

Educators Who Shape Our Community: Honoring 20, 30, and 40 Years at Winsor

Hosted by the Winsor Board of Trustees, the Faculty, Staff, and Trustee Dinner honors Winsor employees celebrating milestone years at the school. The annual dinner is a testament to those who dedicate their careers to Winsor service and the enduring gratitude of the Winsor community to the educators who shape the institution.

All Winsor employees are invited to the festive evening, which begins with a cocktail hour followed by a dinner program, and includes the awarding of the Pennypacker Prize. When employees reach 20 years of service, students, alumnae, and colleagues provide personalized tributes that are collected into a moving account of their Winsor tenure. With friends and family looking on, employees are celebrated with a speech and also receive everyone’s full-length submissions as a keepsake.

This year, four faculty and staff members celebrated 20, 30, and 40 years, representing the World Languages, History, and Science Departments, as well as Model U.N. and Speech and Debate.

Laura Bravo

Over her 20 years, Ms. Bravo has taught every Spanish class Winsor offers. Deeply involved in the Winsor community, she has taught flamenco in the After-School Program and served on the Global Citizenship Committee that developed the Principles of Global Responsibility. She supports students as an advisor to First Generation Experience affinity group and Spanish Club, organizing events such as movie and salsa nights.

During the Covid shutdown in the spring of 2020, Ms. Bravo treated virtual instruction like a performance and transformed her apartment into a stage. She recreated iconic scenes, from Eva Perón’s balcony speech to Andy Warhol’s “Mickey Mouse,” all using household items—her dog even made guest appearances for supporting roles. Her love of the arts, especially dance, has resulted in cross-department collaborations, bringing movement and music to theater productions, choral works, and language classes.

A fearless trip leader, Ms. Bravo has taken Winsor students to Mexico, Cuba, Guatemala, Ecuador, Puerto Rico, and the Dominican Republic. From flamenco stages to the classroom to study-abroad programs, Ms. Bravo has been a source of inspiration and guidance. Rani Balakrishna ’21 fondly describes her teaching “like a warm hug” while Sophia Griffith-Gorgati ’14 commented that learning with Ms. Bravo was not just about mastering Spanish but about becoming a more compassionate global citizen. As Sophia says, “To learn Spanish with Ms. Bravo is to learn how to be a human being in this world.”

Josh Constant

A stalwart of the History Department, Josh Constant’s 20 years at Winsor weren’t always in the classroom.

From club to varsity, Mr. Constant has coached students in basketball, golf, lacrosse, and soccer. He was also the co-chair of the Teaching and Learning Committee for the “Learning in the 21st Century” strategic plan, and then stepped up to co-chair the school’s most recent NEASC accreditation. With a knack for the middle-school years, Mr. Constant has served as a class coordinator for Class II, Class III, and Class IV over the years and is currently the Lower School student-life coordinator and advisor to the Lower School Student Council—all this in addition to his work as a history teacher. To call him an energetic colleague would be an understatement.

In the classroom, from dad jokes to a historical meme competition, Mr. Constant is known for making history come alive. Anya Keomurjian ’16 remembers him as “the first teacher who challenged me from my very first day in Class II. He made history interesting in a way no one ever had before.” Similarly, Tristen Leone ’22, who pursued a classics major in college, credits Mr. Constant for fostering her love for history. She shares, “There is no doubt that Mr. Constant is a reason for my success in college and why I am so excited to continue to study the past in graduate school.”

Denise Labieniec

Affectionately called “Ms. Labin” by students, in her 30 years at Winsor, Denise Labieniec has served as a physics teacher, director of studies, institutional researcher, advisor, Lower School science and STEM faculty, action-research teacher, department head, curriculum committee chair, curriculum review chair, ILE mentor, Upper School class coordinator, faculty chair for the annual fund, chaperone for countless events, organizer for all Science Department bands and performances, and recipient of numerous senior yearbook dedications.

World Languages Faculty Sally Hatcher, who teaches Latin, shared, “one of the official titles for the Roman emperors was ‘primus intus parēs,’ which means ‘first among equals.’…This phrase makes me think of Denise… because of the way she has distinguished herself in all her many roles at Winsor. …The ‘inter parēs’ part is key, though, because Denise never thinks of herself as the first or the best. She is always giving credit to those around her and expanding her circle of influence. She wholeheartedly believes that the strength of Winsor lies in its community.”

Tiferet Levine Gazit ’98 remembers “sitting in a college classroom with only one other female student and thinking, ‘if there were more Ms. Labieniecs in the world, there’d be more girls here.’” Leslie Dewan ’02 shared, “It was because of Ms. Labieniec that I went to MIT and studied nuclear physics. Her love for and skill at communicating science inspired me, and today, one of the most fulfilling parts of my career is public speaking about science and engineering to inspire others. I’m eternally grateful to her.”

Jean Berg

Jean Berg accepted her first Winsor job as a soccer coach in 1985, and it’s a little-known fact that she designed Winsor’s first school bus routes. But the mother of three Winsor alums—Jennifer Berg Bittner ’77, Susan Berg Klein ’81, and Jessica Berg ’85—is most well known for running the Model U.N. and the speech and debate program for much of her 40 years at Winsor.

Ms. Berg teaches students not only how to debate but how to believe in themselves, inspiring generations of Winsor alums and showing students that their voices matter. Her ability to instill confidence in students while also refining their technique has left a lasting mark.

Recalling the “care and coaching” she received at Winsor, Grace Ogilby ’08 said of Ms. Berg, “Her standards for a clean, crisp argument forcefully delivered are the highest of anyone I have ever met—and I say this after having worked as a staffer in the U.S. Senate and a consultant briefing executive teams regularly.”

Ellen Burstein ’18 describes Ms. Berg’s precision, sharing, “Ms. Berg taught us both the techniques of parliamentary debate…and how to carry ourselves as successful debaters—how to trust ourselves, our ideas, and our words.”

Nupur Chaudhury ’01 added, “The foundation that Jean gave me in structuring an argument, staying grounded in my words, and, above all, to believe in what I am presenting still rings true. …I am forever grateful for Jean seeing something in me that I didn’t see in myself, and nurturing this idea that I was important, that I had a point of view, and that I had something to say.”

Mary Butcher Receives Pennypacker Prize

The Pennypacker Prize is awarded each year to a teacher who is in at least their third year of full-time teaching at Winsor. Created in 2002, the award is “given annually in the name of Henriette Pennypacker Binswanger ’52, with respect and admiration for the educational excellence of the Winsor School and the memory of an extraordinary experience.” The award recipient is kept secret until the last possible moment with everyone—including the recipient—guessing who it might be based on clues in the presentation speech.

Mary Butcher received the Pennypacker Prize during the 2024–25 school year, and almost everyone knew right away from Head of School Sarah Pelmas’s opening sentence: “This year’s winner stands out for a variety of reasons, and not simply because of their pink hair, or their rock star flair, or their accent which suggests a non-New-Englander. In fact, the words everyone uses to describe this teacher and their classes are ‘magical’ and ‘authentic.’”

Mx. Butcher, who hails from the U.K. and teaches math, is regarded by colleagues for thoughtful curriculum design and a positive, cheerful attitude.

Mathematics Department Head Laura Cohen sat in on one of Mx. Butcher’s classes, where they introduced the concept of probability to students by throwing a pair

of dice to determine which horse would win a race.

Ms. Cohen shared that classes like this are commonplace, “full of energy and life and happiness, meticulously planned out, though you never see the heavy hand of structure in the way they play out.”

Head of Lower School Sharon Jones Phinney agrees, adding, “They combine fun and guidance with care and candor, going to great lengths to support their students. Their genuine concern for each child is evident.”