Register as an alumni from Winchester High School (Winchester Massachusetts) and reunite with 2,531 classmates and old friends. Share your memories by posting photos or stories, or find out about your next class reunion!
Class Yearbooks
Football
Varsity Football Schedule 2026-27
09/09 vs Lynn Classical
09/17 vs Acton‑Boxborough
09/24 vs Masconomet Regional
10/01 vs Melrose
10/08 vs Reading Memorial
10/15 vs Arlington
10/21 vs Lexington
10/29 vs Belmont
11/25 vs Woburn Memorial
09/17 vs Acton‑Boxborough
09/24 vs Masconomet Regional
10/01 vs Melrose
10/08 vs Reading Memorial
10/15 vs Arlington
10/21 vs Lexington
10/29 vs Belmont
11/25 vs Woburn Memorial
Recently Joined Alumni
Timothy Wood
Class of 1985
Class of 1985
David Cheever
Class of 1976
Class of 1976
Tom Connolly
Class of 1979
Class of 1979
Dana Kelly Jr
Class of 1960
Class of 1960
Alethea Black
Class of 1987
Class of 1987
Linda Cowles
Class of 1973
Class of 1973
Barbara Weber
Class of 1977
Class of 1977
Michael Dellorusso
Class of 1971
Class of 1971
Tom Tom Shirley
Class of 1977
Class of 1977
Jack Kimball
Class of 1965
Class of 1965
Elizabeth Elizabeth Cuff
Class of 1960
Class of 1960
Robert Sousa
Class of 1977
Class of 1977
Winchester Yearbooks
Flip through class yearbooks or browse photo albums from classmates, and see what they look like now:
Winchester Apparel
Check out our huge selection of school spiritwear, including shirts, shorts, accessories and much more!
SHOW YOUR PRIDE
Winchester High School Apparel
Winchester High School Obituaries
