Upcoming Community Events
Tuesday, September 1, 2026
Sep 1 2026 | 7pm: Toastmasters • featureLocation: Winchester Public Library
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Cultural, Education, Community
Wednesday, September 2, 2026
Sep 2 2026 | 12pm: Itsy Bitsy Readers • featureLocation: Winchester Public Library
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Cultural, Education
Sep 2 2026 | 1pm: Itsy Bitsy Readers • featureLocation: Winchester Public Library
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Cultural, Education
Thursday, September 3, 2026
Friday, September 4, 2026
Sep 4 2026 | 10:30am: Shake Rattle and Read • featureLocation: Winchester Public Library
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Cultural, Education
Sep 4 2026 | 3:30pm: Board Game Afternoon • featureLocation: Winchester Public Library
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Cultural, Education
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