The logo of the Winchester Education Foundation represents the four member organizations and the mission of each organization:
- the opened book represents the Winchester Public Schools and its credo, “Learning for all, whatever it takes”;
- the runner represents the Judges Athletic Association and its commitment to serving student-athletes and the athletic program of John Handley High School;
- the architectural column represents the Handley Museum and Archives and its dedication to preserving the history, beauty and cultural significance of John Handley High School;
- and the torch represents the Handley trust and its perpetuation of the legacy of Judge Handley: private support of public education in the City of Winchester.
The logo shares the school colors of John Handley High School: maroon and white.