Cheshire Academy Head of School Named One of Toddle’s 100 Independent School Innovators

CHESHIRE, CT, UNITED STATES, October 23, 2026 /CourierPR/ -- Cheshire Academy, a coeducational college-preparatory boarding and day school for grades 9-12 and postgraduate, has seen its Head of School, Tom Woelper, recognized as one of Toddle’s 100 Independent School Innovators for 2026. This national honor, bestowed by Toddle, an AI-powered teaching and learning platform used by more than 100,000 educators worldwide, acknowledges Woelper’s leadership in strategic planning and schoolwide change.

Woelper was selected in the Leadership & Systems Change category for his work guiding Cheshire Academy’s strategic planning process. The recognition highlights his approach to building a shared vision for the school and translating community input into priorities for its future.

Since joining Cheshire Academy in January 2025, Woelper has led a strategic planning process centered on two crucial questions: "Who are we?" and "Where are we going?" More than 250 members of the school community, including students, faculty, staff, alumni, donors, trustees, families, and friends, contributed their perspectives. Their input informed a refreshed mission statement and a Strategic Plan approved by the Board of Trustees in June 2026.

One of the key initiatives arising from this strategic planning process is Cheshire Academy’s new Purposeful Action Framework, which puts the school’s long-held motto, "ich dien," or "I serve," into practice by making service a more intentional, integrated part of school life. The initiative began with faculty and staff working in small groups on service projects across campus, in Cheshire, and throughout the greater New Haven area during opening meetings.

Founded in 1794, Cheshire Academy is a coeducational college-preparatory boarding and day school for grades 9-12 and postgraduate. With 370 students from 13 states and 18 countries, Cheshire Academy takes a tailored approach, providing students with a wide variety of academic and extracurricular offerings that are optimal to their individual needs, strengths, and interests. Located in Cheshire, Connecticut, the 104-acre campus rests in a quintessential and safe New England community conveniently located between New York and Boston. Cheshire Academy's supportive, one-to-one college counseling program begins early on, resulting in commitments to some of the country's most competitive colleges and universities. With a wide range of programming, Cheshire Academy offers the world-renowned International Baccalaureate, Roxbury Center for Learning & Leadership, and Global Citizenship Diploma Distinction. The Academy is home to 17 athletic teams, with over 30% of student-athletes in the Class of 2025 going on to play at the collegiate level.