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  • ENKA Fair

    Winchester Center Winchester, MA

    The En Ka Fair has been a tradition in Winchester since planning began in 1934. Scheduled for the third weekend in May, it has grown from a single ride and...

  • Winchester’s 43rd Annual Town Day

    Winchester Center Winchester, MA

    Winchester Town Day had its beginning in the mid-1970s when a group of town residents decided that a late spring community party would be a great way to start off...

  • Pridefest 2024

    Town Common Winchester, MA

    Join us for this 4th annual student-organized celebratory and educational festival on the Winchester Town Common. This is a FREE event for families and children of all ages! To volunteer...

  • Porchfest 2024

    The 2024 Winchester Porchfest will be held on: Saturday, June 8, 2024 (rain date June 9) 12noon – 5:30pm Join us for a free community event, full of festive performances...

  • Winchester Farmers Markets

    Town Common Winchester, MA

    Our 2024 season will start Saturday, June 8th and ends Saturday, October 26th. We are open every Saturday (rain or shine) 9:30am-1:30PM at the Winchester Common. The farmers market will...

  • Stroll Week’s “Trolls on the Stroll” Scavenger Hunt

    Winchester Center Winchester, MA

    Find all the Trolls in the stores below and be entered to win “First in line to meet Santa!” Drawing on Sunday, December 8th Ballots available at the following participating...

  • The Chamber’s Annual Holiday House Tour

    Winchester, MA

    Each year the Chamber of Commerce coordinates the Annual Holiday House Tour with beautiful homes that showcase the artistry and creativity of Winchester’s talented residents and get everyone in the...

    $30