Cheshire Academy Leader Selected to Toddle’s 100 Innovative Educators

Tom Woelper of Cheshire Academy named to Toddle's 100 Innovators in Education

Woelper among 100 independent school educators recognized for advancing innovation in the curriculum, AI, and school leadership  Cheshire Academy Head of School Tom Woelper is one of The 100 Independent School Innovators 2026, a select group of school leaders whose work is making learning more meaningful, more equitable, and more future-facing. Recognized by Toddle, a leading AI-powered platform for teaching and learning, Woelper was invited to join those chosen at The Summit, a December gathering for peer exchange […]

Cheshire Academy Marketing Director Featured on FOX61, Yahoo! News

Cheshire Academy's Sarah LeBlond was featured on FOX61 News for her role in Rebellion Group's CT "Off Record" event for marketing leaders

Sarah LeBlond says critical issues discussed at Connecticut marketing event inform Cheshire Academy intern program, support Strategic Plan Cheshire Academy Director of Marketing & Communication Sarah LeBlond shared with FOX61 News in the Sept. 22 “Live at 5” television broadcast the lessons she planned to share at an event for state marketing leaders. Furthermore, she noted the […]

Independent School Magazine Features Cheshire Academy Head Tom Woelper

Woelper discusses his path to Cheshire Academy and what inspires him in the Fall 2026 issue of Independent School Magazine  Recently, Cheshire Academy Head of School Tom Woelper appeared on the National Association of Independent Schools (NAIS) podcast Member Voices to trace his career, how the school is addressing the widespread challenges of financial stability and AI in the space, and the enduring need for empathy and […]

Cheshire Academy Head of School Featured on National Independent School Podcast

Connecticut Boarding School Leader Joins NAIS “Member Voices” to Discuss Navigating a 230-Year-Old Institution Through Uncertainty Cheshire Academy Head of School Tom Woelper P’26 was invited to share his leadership philosophy on Member Voices, the official podcast of the National Association of Independent Schools (NAIS), in an episode released June 1, 2026. The 43-minute conversation […]

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