Convocation Takes to the Skies
Waving traffic batons, donning safety vests, and wearing peaked caps, seniors “flew” into the David E. and Stacey L. Goel Theater to the tune of Sean Kingston’s dance anthem “Fire Burning.”
Head of School Meredith Legg P’32 welcomed everyone to the 2026–27 school year telling students they were “one year older, and one year wiser” before introducing new faculty and staff.
After explaining the role of the corporation to students, Ms. Legg introduced President of the Winsor Corporation Allison Kaneb Pellegrino ’89, P’21, ’22 who offered reflections from her own Winsor journey and drew inspiration from the late great Dolly Parton. Ms. Pellegrino encouraged students to “dream big, stay kind, and don’t let anyone tell you that you have to choose between being nice and being unstoppable.”
Before offering advice to Classes I through VIII, President of COLLECT Meryl Sutich ’27 got sentimental: “The ringing of Miss Winsor’s bell marks the beginning of the end for the Class of 2027,” she said. Meryl advised Class I to “be open to everything, talk to everyone, and try everything.” Offering pearls of wisdom about friendship, kindness, and bravery, each grade received suggestions for how to make the most of the year ahead. For Class V, Meryl—who picked up a field hockey stick for the first time as a freshman—had particularly poignant advice, “not everything comes naturally at first, but it’s very important to try.” Now as a senior on the varsity squad, Meryl shared, “never let a fear of asking for help prevent you from succeeding.”
Senior Class President Emma Rothman ’27 officially announced the senior’s theme: Now Boarding Flight 2027. She welcomed everyone “aboard” the new school year and told new students, “buckle up, you’re going to have an amazing journey here.” Calling a Winsor education a passport to the world, she encouraged everyone to “collect new passport stamps” by trying a new sport or making a new friend. Naming the interconnected support structures at Winsor, like flight attendants, flight crew, and the control tower—referring of course to friends, club co-heads, discussion leaders, and others—she said, “we wouldn’t be able to lift off without them.” Likening Winsor to an airport where people come together, she explained that everyone at an airport has the same goal, to reach their destination. “Our shared goal, graduation, has united us over the last 7 years,” she said, but “what our class understands is that high school is not an individual experience. We do so much better when the people around us are doing well too.”
Heads of Lower School Council Alex Chen ’31 and Shylee Feingold ’31 offered their own words of wisdom and told students to “find the courage to take risks,” emphasizing that “the entire Winsor community has your back.” To the seniors they said, “everyone is looking up to you. We hope you have a school year with unforgettable moments.”
The final speaker of Convocation, Ms. Legg emphasized the difference between “productivity mode” and “present mode.” Sharing that she too is susceptible to an internal “productivity alarm clock,” she recalled a moment this summer, when, on a bucket-list summer trip to the Galapagos Islands, in the middle of the Pacific Ocean, 3,000 miles from Pilgrim Road, she had to actively remind herself to be present. Switching on “present mode” looks like making connections, reflecting on experiences, or sitting quietly. “I hope you will find time for the many small moments of being present,” said Ms. Legg, who encouraged students, faculty, and staff alike to find moments of presence and reflection this school year—something that requires practice and discipline in the modern world.
Amid the hustle and bustle of the school year, “it could be as simple as taking five minutes to stare out the bus window on the ride home or sit quietly noticing the world around you while you wait for your ride to pick you up after school. It’s as simple as listening to a speaker during assembly. Or pausing during a free period to just listen to a friend talk about their day. It’s taking a walk with a family member in the evening and sharing your day,” she explained.
Convocation closed with everyone on their feet. Students Advocating School Spirit (SASS), had the gathered assembly stomping and clapping along to two classic school chants—“Red Hot” and “Hey All You Winsor Fans”—while Head of Performing Arts Felicia Brady-Lopez and Choral Director Andrew Marshall led everyone in singing “Jerusalem” by C. Hubert Parry.
To officially start the school year, Lower School Council Heads Alex and Shlyee rang Miss Winsor’s bell. The gentle chime has opened and closed each school year since 1910.
