Upcoming Community Events
Monday, August 31, 2026
Tuesday, September 1, 2026
Sep 1 2026 | 7pm: Toastmasters • featureLocation: Winchester Public Library
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Cultural, Education, Community
Wednesday, September 2, 2026
Thursday, September 3, 2026
Saturday, September 5, 2026
Sep 5 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Sunday, September 6, 2026
Saturday, September 12, 2026
Sep 12 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Wednesday, September 16, 2026
Sep 16 2026 | 12am: Webinar: AI SEO: Get Your Brand Seen and Chosen Online • feature
√ Online
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Commercial
Thursday, September 17, 2026
Sep 17 2026 | 8pm: Early Release (Preschool-Grade 12): WPS Professional Development • feature
WPS
Education
Saturday, September 19, 2026
Sep 19 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Tuesday, September 22, 2026
Sep 22 2026 | 6:30pm: League of Women Voters of Winchester's Civic Leadership Award ☆Location: Lynch Elementary School
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Community
Saturday, September 26, 2026
Sep 26 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Saturday, October 3, 2026
Oct 3 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Thursday, October 8, 2026
Oct 8 2026 | 8pm: Early Release (Preschool-Grade 12): WPS Professional Development • feature
WPS
Education
Saturday, October 10, 2026
Oct 10 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Oct 10 2026 | 9:30am: International Day at the Farmers' Market • featureLocation: Town Common
Cultural, Family
Sunday, October 11, 2026
Wednesday, October 14, 2026
Saturday, October 17, 2026
Oct 17 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Tuesday, October 20, 2026
Saturday, October 24, 2026
Oct 24 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Saturday, October 31, 2026
Oct 31 2026 | 9am: Winchester Farmers Market • featureLocation: Town Common
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Cultural, Education, Environment, Family, Health, Community
Monday, November 2, 2026
Tuesday, November 10, 2026
Saturday, November 21, 2026
Nov 21 2026 | 10am: Winchester Open Studios and Art Sale ☆
Several locations around Winchester
Commercial, Cultural
Tuesday, November 24, 2026
Wednesday, November 25, 2026
Tuesday, December 22, 2026
Wednesday, December 23, 2026
Sunday, December 27, 2026
Tuesday, January 12, 2027
Jan 12 2027 | 7pm: Early Release (Preschool-Grade 12): WPS Professional Development • feature
WPS
Education