New traditions, speeches, songs, and a name for the Cheshire Academy Cat mark annual ceremony on Simosa Field
Cheshire Academy opened its 2026-27 academic year on Monday, September 7, with a lively Convocation, featuring songs and speeches from students, and the unveiling of the school mascot’s forever name. A large crowd of family, friends, and alumni attended the event under picture-perfect skies.
The 233-year-old school, the 11th oldest boarding school in the country, welcomed 360 students from 24 states and 15 countries, including Australia, Brazil, Sierra Leone, Tajikistan, Vietnam, and Jamaica.
Student Body President Matthew “Tre” Roscoe ’27 looked to Spiderman for inspiration, reminding fellow students that “with great power comes great responsibility.
“Everyone on this field is responsible for what this year amounts to, and I genuinely believe we can have one of the best years in Cheshire Academy history,” said the Cheshire resident, who plays football and is earning the Global Citizenship Diploma Distinction. “We have the power to make change and with that power, we must be responsible and use it for good.”
Seniors Wyatt Brandt, Sebastian Cebada-Montemayor, Patricio Cebada-Montemayor, and Maya Harris sang “Everybody Wants to Rule the World, and The 1794s, CA’s a cappella group, started the ceremony with “The Star-Spangled Banner.”
Head Prefects Xiyue “Eleanor” Zhang ’27, of Shenzhen, China, and Sebastian Cebada-Montemayor ’27 of Cancun, Mexico, both offered encouraging words before Head of School Tom Woelper took the podium for his remarks. He touched on the South African concept of “ubuntu,” a word that captures one of Cheshire Academy’s core values, Belonging.
“I am because we are,” he told the students. “In other words, you do not become part of a place only by deciding it yourself. You become part of it because other people make room for you and call you one of their own.”
As if to illustrate the concept, this year’s ceremony included an induction ceremony, as each new student in every grade was presented with a Cheshire Academy crest patch to wear proudly on their blue blazers at formal events and the school’s Traditional Tuesdays.
“You receive this crest today, at the very beginning of your time here – not after you have earned your place, but as a sign that you already have one,” said senior faculty member and French teacher Laura Longacre. “From this day forward, you belong to Cheshire Academy, and Cheshire Academy belongs, in part, to you.”
Woelper also reminded seniors gathered that they will soon be part of a new tradition started by the Class of 2026, who painted a prominent rock on nearby Sevigny Field with their names before their graduation day. The Class of 2027 will paint over those names with their own next spring to signify the passage of time and the connection with all the ‘layers’ of the Cheshire Academy community.
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 got acclimated through orientation sessions and joined day and domestic boarding students for events emphasizing the school’s core values of Belonging, Engagement, Collaboration, and Growth.
Naming the Cat
Near the end of the ceremony, Woelper announced something that has been in the works for months: the naming of The Cat, Cheshire’s mascot. While the cat has been around since the 1950s, it has never had a formal name. Members of the Cheshire Academy community – students, faculty, staff, alumni, and friends – voted on several possible monikers over the summer, narrowing it down to the chosen few. A cheer went up when Woelper announced the winner: Bowdie – for Bowden Hall, the oldest schoolhouse in continuous use in Connecticut, and the Rev. John Bowden, the Academy’s first headmaster.
Woelper encouraged the whole community to look to the school’s traditions and its forward-thinking values as they move through 2026-27.
“Welcome to the 233rd year, Cats,” he said. “Wear the patch well. Carry the tradition forward. And let us make this year worth painting over.”
