The Community Calendar is to publicize events located in Winchester where the pubic is invited to attend. For profit businesses are allowed to post on this calendar up to 3 days per month. All submissions are subject to approval.

No holidays, events outside of Winchester or personal events are to be posted.

Community Calendar

  1. FAN Pride Window Painting

    May 25, 2023 - May 31, 2023
    Throughout Downtown

    FAN - Family Action Network of Winchester, MA is hosting our Second Annual PRIDE Window painting for June. This year we have even more amazing businesses hosting windows and space to spread more joy. Thanks so much to all of our participants. Registration is now open to the public and we would love if you, your elementary, middle and high schoolers would help us by signing up to participate. All information is in the event here. We will email out window assignments as we get more registrants. We ask all painters to complete their work by May 31st (plenty of time before and after the long weekend) to get Winchester ready for a beautiful June! We anticipate that windows will stay up through mid-June this year. If you have any questions, please reach out to

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  2. 2023 Winchester Tennis Association Donnie Ellis Spring Draw Tournament

    May 29, 2023, 8:00 AM - 6:00 PM

    This Tournament is a blind draw where the WTA will match individuals for doubles draws with the exclusion of Family Doubles. It is one of the many great opportunities players have to meet one another in the community.

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    May 29, 2023, 9:15 AM - 10:30 AM

    Parade starts at WHS

    The parade will step off at 9:15am, northbound (right) on to Skillings Road. It will take a left on Main Street, right on Church Street, left on Waterfield Road left on Mystic Valley Parkway, and pause to place a wreath at WWI Memorial. The parade will continue down Main Street and take a right on Mt. Vernon Street. It will pause again in front of the Public Safety Building then continue to Edward F. O’Connell Memorial Plaza for civic exercises. Scroll for more information.

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