Ian Wildermann, ’03, M.S. ’10, SYC ’21, a three-time Southern Connecticut State University alumnus and longtime educator at Cheshire High School, has been named Cheshire Public School’s 2026 Teacher of the Year.
Wildermann earned both his bachelor’s and master’s degrees in English from Southern, graduating in 2003 and 2010, respectively, before returning to earn a Sixth-Year Certificate in Educational Leadership in 2021. He has taught English at Cheshire High School since 2010 and has served as chair of the school’s English Department since 2015.
Currently teaching juniors and seniors, including AP Language and Composition and UConn Early College Experience British Literature, Wildermann has built his approach around challenging students to think deeply, take creative risks, and focus on their development as thinkers and writers.
Described by his students as a “warm demander,” Wildermann emphasizes meaningful, complex work rather than assignments centered on checklists or busywork. His students are encouraged to make deliberate choices based on their audiences and to view learning as a process of growth rather than simply a path toward a grade.
Beyond the classroom, Wildermann plays an active role in professional development for fellow educators. During the past year, he helped design and facilitate workshops focused on “Building Thinking Classrooms” and “Student Voice,” with an emphasis on strengthening instruction and creating opportunities for students to have a greater role in their education.
His work also addresses one of the most rapidly evolving issues facing educators: artificial intelligence. Wildermann advocates for helping students learn to use AI responsibly and ethically while continuing to develop their own critical thinking, creativity, and individual voices.
As Teacher of the Year, Wildermann has emphasized the importance of educators’ work amid those changes.
“I am not daunted by the challenges we face as teachers; I am inspired,” Wildermann said. “Inspired knowing that our job … is as important, and as critical, as it has ever been.”
The Cheshire District Teacher of the Year is selected through a process that includes community nominations, an administrative review of applications and interviews with a committee of district leaders and previous Teacher of the Year recipients.
Wildermann’s recognition adds another chapter to a career in education shaped in part by his time at Southern and now dedicated to helping the next generation of students become stronger, more thoughtful learners.
