Upcoming Community Events
Tuesday, May 19, 2026
Wednesday, May 20, 2026
May 20 2026 | 12pm: Itsy Bitsy Readers • featureLocation: Winchester Public Library
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Cultural, Education
May 20 2026 | 1pm: Itsy Bitsy Readers • featureLocation: Winchester Public Library
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Cultural, Education
May 20 2026 | 3:30pm: Books & Building • featureLocation: Winchester Public Library
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Cultural, Education
May 20 2026 | 5:30pm: Celebrate Winchester: Community and Business Awards • featureLocation: Griffin Museum of Photography
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Commercial
May 20 2026 | 7:30pm: VIRTUAL: For High School Juniors: Creating a Compelling College Application this Summer • featureLocation: Winchester Public Library
√ Online
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Cultural, Education
Thursday, May 21, 2026
May 21 2026 | 11am: Pattycake Place • featureLocation: Winchester Public Library
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Cultural, Education
May 21 2026 | 3:30pm: Bracelet Buddies • featureLocation: Winchester Public Library
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Cultural, Education
May 21 2026 | 7pm: Friends of the Library meeting • featureLocation: Winchester Public Library
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Cultural, Education, Community
Friday, May 22, 2026
May 22 2026 | 10:30am: Shake Rattle and Read • featureLocation: Winchester Public Library
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Cultural, Education
May 22 2026 | 3:30pm: Board Game Afternoon • featureLocation: Winchester Public Library
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Cultural, Education
Saturday, May 23, 2026
May 23 2026 | 8am: 2026 Donnie Ellis Spring Draw Tennis Tournament ☆Location: Packer-Ellis Tennis Courts
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Athletics
May 23 2026 | 10:30am: Family Storytime and Parachute Games • featureLocation: Winchester Public Library
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Cultural, Education
Monday, May 25, 2026
Tuesday, May 26, 2026
May 26 2026 | 10:30am: Step into Storytime • featureLocation: Winchester Public Library
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Cultural, Education
Wednesday, May 27, 2026
May 27 2026 | 12pm: Itsy Bitsy Readers • featureLocation: Winchester Public Library
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Cultural, Education
May 27 2026 | 1pm: Itsy Bitsy Readers • featureLocation: Winchester Public Library
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Cultural, Education
May 27 2026 | 3:30pm: Books & Building • featureLocation: Winchester Public Library
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Cultural, Education
Thursday, May 28, 2026
May 28 2026 | 11am: Pattycake Place • featureLocation: Winchester Public Library
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Cultural, Education
May 28 2026 | 11am: Sociological Book Group @ The Jenks • featureLocation: Jenks Center
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Cultural, Education
Thursday, June 4, 2026
Sunday, June 7, 2026
Wednesday, June 10, 2026
Jun 10 2026 | 3pm: AI Marketing Webinar: Generate Better Leads With SEO, AI Search (GEO) & Content • feature
Brick Marketing Free Webinar 101 Federal Street Suite 1900 Boston MA 02110
Commercial
Saturday, June 13, 2026
Jun 13 2026 | 9am: Opening Day at the Farmers Market • featureLocation: Town Common
Commercial, Community, Cultural
Monday, June 15, 2026
Jun 15 2026 | 12pm: Winchester Special Education Parent Advisory Council (WinPAC) Meeting • feature
WPS
Education, Government
Thursday, June 18, 2026
Tuesday, June 23, 2026
Jun 23 2026 | 8pm: Early Release: Preschool: 11:05 a.m., K-5: 11:25 a.m., McCall, WHS: 12 p.m. • feature
WPS
Education