Teacher Of The Year Announced In Cheshire

CHESHIRE, CT — Ian Wildermann has been named the Cheshire Public School District’s 2026 Teacher of the Year, officials announced Thursday.

Wildermann has served as an English teacher at Cheshire High School since 2010 and stepped into the role of English Department Chair in 2015.

Currently teaching 11th and 12th grades, including AP Language and Composition and UCONN ECE British Literature, Wildermann is known by his students as a “warm demander,” according to a news release.

“His teaching philosophy focuses on creating an environment where students are not burdened by busywork or checklists, but are instead challenged by the complexity of tasks,” according to the news release. “He encourages students to take creative risks, make deliberate choices based on their audience, and focus on their growth as thinkers rather than simply earning a grade.”

Read more from the news release below:

In addition to his classroom impact, Wildermann is a dedicated educational leader who regularly designs and facilitates professional development. In the past year, he has co-designed workshops for teachers on "Building Thinking Classrooms" and "Student Voice," aiming to improve high-quality instruction and give students a greater say in their education.

Wildermann is also deeply engaged with modern educational challenges, particularly the rise of artificial intelligence. He advocates for teaching students how to use AI responsibly and ethically while maintaining their own critical thinking and creativity. His overarching message as the 2026 Teacher of the Year is one of inspiration in the face of modern challenges: "I am not daunted by the challenges we face as teachers; I am inspired. Inspired knowing that our job... is as important, and as critical, as it has ever been.”

Wildermann holds a Bachelor of Arts, a Master of Science in English, and a Sixth-year Certificate in Educational Leadership, all from Southern Connecticut State University.

The Cheshire District Teacher of the Year is selected through a rigorous process that includes nominations from the community, an application review by the administration, and interviews with a committee of district leaders and former Teacher of the Year winners.