Upcoming Community Events

Monday, October 19, 2026

Event Flier
Oct 19 2026 | 6:30pm: Invasive Species Detection Dogs: Pets Trained To Save New England From The Spotted Lantern Fly • feature
http://winpublib.org
Location: Winchester Public Library
L
Cultural, Education
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Tuesday, October 20, 2026

Oct 20 2026 | 8pm: Early Release (PK-5): Conferences • feature
https://www.winchesterps.org/
WPS
Education
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Thursday, October 22, 2026

Event Flier
Oct 22 2026 | 5pm: Flu & COVID Clinic ☆
https://www.winchester.us/1062/Board-of-Health
Location: Jenks Center
Community
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Saturday, October 24, 2026

Oct 24 2026 | 9am: Winchester Farmers Market • feature
https://www.wfmchub.org
Location: Town Common
T
Cultural, Education, Environment, Family, Health, Community
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Sunday, October 25, 2026

Sanborn House
Oct 25 2026 | 2pm: Celebrating 20 years as Stewards of the Sanborn House • feature
http://www.winchesterhistoricalsociety.org
Location: Sanborn House
Cultural
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Tuesday, October 27, 2026

Flier for Carriage House Information Session
Oct 27 2026 | 7pm: Carriage House Information Session ☆
http://www.winchesterhistoricalsociety.org
Location: Sanborn House
Cultural
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Saturday, October 31, 2026

Oct 31 2026 | 9am: Winchester Farmers Market • feature
https://www.wfmchub.org
Location: Town Common
T
Cultural, Education, Environment, Family, Health, Community
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Monday, November 2, 2026

Nov 2 2026 | 7pm: No School | WPS Staff Professional Development • feature
https://www.winchesterps.org/
WPS
Education
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Tuesday, November 10, 2026

Nov 10 2026 | 7pm: No School • feature
https://www.winchesterps.org/
WPS
Education
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Wednesday, November 18, 2026

Flier for American Calliope: Mercy Otis Warren & the Writings of the Revolution
Nov 18 2026 | 7pm: American Calliope: Mercy Otis Warren & the Writings of the Revolution • feature
http://www.winchesterhistoricalsociety.org
Location: Sanborn House
Cultural
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Saturday, November 21, 2026

Winchester Open Studios logo
Nov 21 2026 | 10am: Winchester Open Studios and Art Sale ☆
http://winchesterculturacouncil.org
Several locations around Winchester
Commercial, Cultural
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Tuesday, November 24, 2026

Nov 24 2026 | 7pm: Early Release (Preschool-Grade 12) • feature
https://www.winchesterps.org/
WPS
Education
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Wednesday, November 25, 2026

Nov 25 2026 | 7pm: No School: Thanksgiving • feature
https://www.winchesterps.org/
WPS
Education
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Tuesday, December 22, 2026

Dec 22 2026 | 7pm: Early Release (Preschool-Grade 12) • feature
https://www.winchesterps.org/
WPS
Education
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Wednesday, December 23, 2026

Dec 23 2026 | 7pm: No School: Winter Break • feature
https://www.winchesterps.org/
WPS
Education
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Sunday, December 27, 2026

Dec 27 2026 | 7pm: No School: Winter Break • feature
https://www.winchesterps.org/
WPS
Education
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Tuesday, January 12, 2027

Jan 12 2027 | 7pm: Early Release (Preschool-Grade 12): WPS Professional Development • feature
https://www.winchesterps.org/
WPS
Education
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Sunday, January 17, 2027

Jan 17 2027 | 7pm: No School • feature
https://www.winchesterps.org/
WPS
Education
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Monday, January 18, 2027

Jan 18 2027 | 7pm: Early Release (Grades 6-8): Conferences • feature
https://www.winchesterps.org/
WPS
Education
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Sunday, February 7, 2027

Feb 7 2027 | 7pm: 2027-2028 School Year Registration Begins • feature
https://www.winchesterps.org/
WPS
Education
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Sunday, February 14, 2027

Feb 14 2027 | 7pm: No School: February Break • feature
https://www.winchesterps.org/
WPS
Education
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Monday, March 1, 2027

Mar 1 2027 | 7pm: No School | WPS Staff Professional Development • feature
https://www.winchesterps.org/
WPS
Education
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Wednesday, March 10, 2027

Mar 10 2027 | 7pm: WFEE Trivia Bee • feature
https://www.winchesterps.org/
WPS
Education
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Tuesday, March 16, 2027

Mar 16 2027 | 8pm: Early Release (PK-5): Conferences • feature
https://www.winchesterps.org/
WPS
Education
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Thursday, April 1, 2027

Apr 1 2027 | 8pm: Early Release (Preschool-Grade 12): WPS Professional Development • feature
https://www.winchesterps.org/
WPS
Education
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Sunday, April 18, 2027

Apr 18 2027 | 8pm: No School: April Break • feature
https://www.winchesterps.org/
WPS
Education
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Thursday, May 6, 2027

May 6 2027 | 8pm: Early Release (Preschool-Grade 12): WPS Professional Development • feature
https://www.winchesterps.org/
WPS
Education
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Wednesday, May 26, 2027

May 26 2027 | 8pm: Early Release (Preschool-Grade 12): WPS Professional Development • feature
https://www.winchesterps.org/
WPS
Education
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Sunday, May 30, 2027

May 30 2027 | 8pm: No School • feature
https://www.winchesterps.org/
WPS
Education
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Monday, May 31, 2027

May 31 2027 | 8pm: Bus Registration Begins • feature
https://www.winchesterps.org/
WPS
Education
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Wednesday, June 16, 2027

Jun 16 2027 | 8pm: Last Day of School (with no closure days) | Early Release (Preschool-Grade 12) • feature
https://www.winchesterps.org/
WPS
Education
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Thursday, June 17, 2027

Jun 17 2027 | 8pm: No School • feature
https://www.winchesterps.org/
WPS
Education
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Sunday, June 20, 2027

Jun 20 2027 | 8pm: Make-Up Days • feature
https://www.winchesterps.org/
WPS
Education
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Thursday, July 8, 2027

Jul 8 2027 | 8pm: Bus Registration Closes • feature
https://www.winchesterps.org/
WPS
Education
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