Register as an alumni from Winchester High School (Winchester Massachusetts) and reunite with 2,488 classmates and old friends. Share your memories by posting photos or stories, or find out about your next class reunion!
Winchester Distinguished Alumni
Here are our special Distinguished Alumni, who we are honoring for their contributions to the site, thank you for your support!
John Urmson
Class of 1961
Class of 1961
Michael Canavan
Class of 1970
Class of 1970
Ellen Guthrie
Class of 1976
Class of 1976
Stephanie Dunn
Class of 2004
Class of 2004
Doug Smith
Class of 1963
Class of 1963
Winchester Past Reunions
Browse through past Winchester High School events to reminisce as you view photos taken at our reunions:
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
Recently Joined Alumni
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
Betty Lou Martensen
Class of 1954
Class of 1954
Andrew Wilsack
Class of 1979
Class of 1979
Find Classmates Winchester High School in Your Class
Winchester High School Football Results - 2025 Season
| Date | Opponent | Result |
|---|---|---|
| 09/11 | Peabody Veterans Memorial (home) | 42-7 (win) |
| 09/18 | Waltham (away) | 42-7 (win) |
| 09/25 | Masconomet Regional (home) | 56-22 (win) |
| 10/02 | Wakefield Memorial (away) | 42-7 (win) |
| 10/09 | Reading Memorial (home) | 42-14 (win) |
| 10/16 | Arlington (away) | 35-21 (win) |