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Save the Date: Holly Jolly Celebration
Come spend some time in Old Town this holiday season during our Holly Jolly Celebration on December 8th! Enjoy caroling and holiday activities including free holiday wagon rides from 1-3 p.m. Specials at shops and restaurants all day. New this year, from 11 a.m.-3 p.m. shop at the Holly Jolly Market for locally made decorative...
Old Town Holiday Parade
Celebrate the fun and excitement of the holiday season in Old Town Winchester. Bands, floats, and specialty units along with Santa will be coming to see you. Don’t forget the tree lighting ceremony, immediately following the parade. The Old Town Christmas Parade begins on November 26th at 7pm and lasts until about 8pm. The parade...
Explore Old Town With Traipse Scavenger Hunts!
Think you know Old Town Winchester? Test your knowledge with 8 free historic scavenger hunts through the Traipse app! About the Traipse App: Traipse is an application program for smartphones and tablets that leads users on a city walking tour that includes both historic landmarks and local businesses. Users choose when to do a Traipse...

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