MAR. 18, 2026 — Wilton Public School officials announced this afternoon that Wilton High School Principal Dr. Bob O’Donnell will retire at the end of this school year, effective Jun. 30, 2026.
O’Donnell has served as WHS principal for 15 years and associate principal for seven years prior to that.
A press release sent by Wilton’s Assistant Superintendent for Human Resources and General Administration Maria Coleman lauded O’Donnell for his “long and successful tenure in the Wilton Public Schools.”
Superintendent Kevin Smith also offered high praise for O’Donnell.
“Bob has been an exceptional high school leader over the past two decades. He is one of the finest educators I have had the privilege of knowing and will be deeply missed,” Smith said.
Calling him a transformational leader, the press release said O’Donnell “support[ed] students and staff in numerous initiatives, including: the cellphone-free high school, the addition of more than 50 new courses to the program of studies, the implementation of the block scheduling model, the New England Association of Schools and Colleges accreditation processes, and the expansion of the co-curricular, fine and performing arts, and athletics programs.”
Coleman described O’Donnell’s 22 years of service to Wilton’s students and families as a period “defined by his commitment to ensuring a safe and welcoming environment for all students, his dedication to upholding Wilton High School’s long-standing tradition of excellence, and his belief that the students and staff of Wilton are among the best in the country.”
Prior to his time in Wilton, O’Donnell began his career as a teacher and resident counselor at the American International School in Salzburg, Austria, where he later became the dean of students. He also served as the global language department chair at the Canterbury School in New Milford, CT and as an assistant principal at Cooper High School in New Hope, MN.
According to the press release, O’Donnell said that “his wish has been for all students to enjoy their high school experience and cherish fond memories as Wilton High School Warriors.”
Wilton Public Schools will post the vacancy for this position this week as the first step to find O’Donnell’s successor.