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Winchester’s 2023 Holiday Stroll Weekend

08 November 2023

2nd Annual Gingerbread House Decorating Contest

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$25.00
25 November 2023

Red Ticket Raffle

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27 November 2023

3rd Annual Holiday Stroll Full Schedule

To print the full schedule, click here

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Winchester Center, Winchester, MA 01890
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27 November 2023

“Trolls on the Stroll” Scavenger Hunt

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Winchester Center, Winchester, MA 01890
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30 November 2023

Battle of the Bartenders

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First House Pub, 528 Main Street
Winchester, MA 01890
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01 December 2023

Book Ends’ “Author Meet & Greet” with Winchester native Matt Tavares

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Book Ends, 559 Main Street
Winchester, MA 01890 United States
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01 December 2023

Annual “Lighting of the Trees” Celebration- Town Common

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Town Common, Winchester, MA
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02 December 2023

Ballet Arts Centre “Nutcracker Suite”

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02 December 2023

“Best in Stroll” Dog Show

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Town Common, Winchester, MA
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02 December 2023

Book Ends’ 2nd Annual Yule Ball

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3rd Annual Winchester Stroll Week