Heartfelt speeches and song mark annual ceremony on Simosa Field
Cheshire Academy opened its 2025-26 academic year on Sept. 7 with a lively Convocation, featuring songs and speeches from students, advice from Head of School Tom Woelper P’26, and wise words from a longtime employee, parent, grandparent, and friend.
The 232-year-old school, the 11th oldest boarding school in the country, welcomed 395 students from 13 states and 18 countries, including Bermuda, China, Finland, Japan, Kazakhstan, and Sierra Leone.
Reflecting on what she would say to her classmates, Nia Jackson ’26, said she saw Cheshire Academy as a watershed, “a place where many different bodies of water meet and flow together, creating something far greater than any single source on its own.”
Jackson, head prefect and a captain of the Varsity Girls Soccer team, was one of several students participating in Convocation. Seniors Abigail Frempong and Aiden Connor sang “A Bridge Over Troubled Water,” and The 1794s, CA’s a cappella group, started the ceremony with The Star-Spangled Banner. Student Council President Zhouran “Cody” Xu ’26 addressed the crowd, speaking of his journey from Tongling, China, to playing lacrosse – and sometimes barber for his friends – at Cheshire Academy.
“All these things came from curiosity, courage, and saying yes to opportunities, and trying to build our own legacy,” he told his fellow students.
Barbara Vestergaard P’96,’02, GP’26, constituent engagement and annual giving officer, offered her thoughts on two of CA’s core values, Belonging and Engagement. Beginning her association with the school as a dorm parent in the 1970s, she has worn many hats at Cheshire – from time as public relations, alumni, and annual fund director to managing the database, planning and events, and the development office and serving as assistant to the associate headmaster.
Beginning her last year as a full-time employee, Vestergaard encouraged the students to “experience it all.
“You may not realize how special these moments are when you’re living them, but I guarantee you will look back fondly at egg sandwiches made with love by Pat or walking the haunted trail with your friends,” she said. “Cheshire Academy will always be your home away from home – there will always be someone here to welcome you back and show you around, but this is your last chance to experience this place as a student. Soak it all in.”
Convocation capped off Opening of School Week, days of preparation for the year ahead. Student athletes completed pre-season training for football, soccer, and volleyball and teachers readied their rooms and met their new students and CA families at events across campus. New international students enjoyed several orientation sessions and day and domestic boarding students enjoyed several events emphasizing the school’s core values of Belonging, Engagement, Collaboration, and Growth.
Woelper concluded the evening by walking through the school’s refreshed mission statement: “Cheshire Academy challenges and supports individual students in developing their character, critical thinking, and confidence to flourish as purposeful global citizens.” Created with input from across the CA community, the mission ‘s well-considered words and the school’s core values continue “a story that has always been about both the individual and the global,” Woelper said.
“Individual growth. Global purpose. These are not competing goals. They are complementary callings,” he said. “So, let’s embrace this year with energy and courage. Let’s build our legacy. Let’s make this year extraordinary together.”
