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This Calendar is to publicize any event, located in Winchester, sponsored by a non-profit or for-profit organization running a fundraiser, where the public is invited to attend. No holidays, events outside Winchester or personal events are to be posted. View All Calendars is the default. Choose Select a Calendar to view a specific calendar. Subscribe to calendar notifications by clicking on the Notify Me button, and you will automatically be alerted about the latest events in our community.

Community Calendar


    October 1, 2021 - October 31, 2021 @

    Your house!

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  2. WORLD OF ORCHIDS: The Caribbean - Massachusetts Orchid Society Annual Show and Sale

    October 22, 2021, 12:30 PM - October 24, 2021, 4:00 PM @

    Sons of Italy Winchester


    Escape to beaches and natural beauty, the Caribbean is the native habitat of thousands of diverse and captivating orchid species. Hosted by the Massachusetts Orchid Society, the theme of the 2021 Show is "The Caribbean" featuring over 20 displays of orchids from national vendors, New England orchid societies and private collectors. Come enjoy the sights and scents of these exotic flowers. The show will feature something for every level of orchid enthusiast, from beginner to advanced, including tours of the displays, plant raffles, and vendors of specialty orchids and growing supplies. The show is $10 per person, with MOS members and children under ten, free. Show times are Friday, October 22 to Sunday, October 24, at the Sons of Italy Hall at 117 Swanton St. in Winchester. For more information please visit Masks required.

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    October 23, 2021, 9:00 AM - 1:00 PM @

    Outside the Transfer Station

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  4. Winchester Farmers Market

    October 23, 2021, 9:30 AM - 1:30 PM @ Town Hall parking lot

    Winchester Farmers Market is open every Saturday through the end of October from 9:30 to 1:30. SNAP customers are welcome and SNAP purchases will be matched up to $15/purchase/day. HEALTH GUIDELINES Covid restrictions have eased but some guidelines remain in place to provide a safe and friendly experience for all. -The 9:30 to 10:00 period will be prioritized for seniors and other vulnerable individuals. -Masks are optional, but please consider wearing one. -Unvaccinated individuals are encouraged to continue wearing masks, in line with CDC and Massachusetts advisories. -Hand sanitizer will be offered on site. -There will be a perimeter around the market with one entrance and one exit. Thirty full- and part-time vendors will be at the market this season. The part-time vendor schedule can be found on the Winchester Farmers Market website and in our weekly newsletters.

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  5. Introduction to Leading Facilitation & Dialogue

    October 23, 2021, 10:00 AM - 12:00 PM

    Oct 23 and Nov 6: We are once again offering Introduction to Leading Facilitation & Dialogue, one of the Network's signature trainings. The purpose of this beginner’s workshop is to empower community members to better navigate difficult conversations. Participants will improve their public speaking and leadership skills while practicing and receiving feedback from experienced instructors. Complete this short form ( to reserve your spot today!

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  6. FREE Happy Halloween Party

    October 23, 2021, 11:00 AM - 11:45 AM @

    Stage Music Center in Winchester MA

    YOU ARE INVITED TO FREE HAPPY HALLOWEEN PARTY! Come in dressed up, bring your friends and let's have a blast! Ages 1,5 - 3,5 years SPOTS ARE LIMITED! Pre-registration is required! Please feel free to contact us if you need any further information: Tel: (781) 570-2556 E-mail:

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