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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

  1. Turkey Trot

    November 24, 2022, 8:00 AM - 11:00 AM
    109 Skillings Road

    The En Ka Society of Winchester will host its 3rd Annual 5k/3.1 m “Turkey Trot” on Thanksgiving morning at 8AM, beginning at the Jenks Center 109 Skillings Road in Winchester. Start a new Thanksgiving tradition for the whole family. You can walk, trot or run the race before you stuff your face! Register now at Registration includes a t-shirt, while supplies last. See you there! For more information, please visit

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    November 24, 2022, 10:30 AM - 12:30 PM

    Knowlton Stadium

    The annual Winchester vs Woburn Thanksgiving Day football game! Tickets sold online at (search for Winchester High School)

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