As an educator with 32 years in middle level education, Winton was fortunate to teach social studies, mathematics, science, language arts as well as working as an enrichment specialist prior to spending 18 years as Principal and House Principal at Bay Trail Middle School in Penfield, NY. During his career he served in union leadership roles and as a trainer for various educational programs.   Winton proudly celebrated Bay Trail Middle Schools designation as a National School To Watch with his staff, students and community in 2010 and their re-designations in 2013, 2016 and 2019. After retiring in 2022, he serves as the Director of Logistics and School Outreach for Sweethearts and Heroes and remains active as a member of the New York State Middle School Association Board, the New York Essential Elements Schools To Watch Leadership Board, and the National Form to Accelerate Middle Grades Reform Board of Directors.