Winter in Woodstock

Experience the MAGIC!

Woodstock, voted one of the TODAY show's "Merriest Main Streets" in the country in 2022 is ready to welcome residents and visitors alike.

Kick off the holiday season with Lighting of the Square on the Friday after Thanksgiving, to our Annual Groundhog Days celebration on February 2, and countless events and activities inbetween!

Special Events this Season

Lighting of the Square
November 24 from 4:00 - 8:00 pm

Visit the historic Square on the Friday after Thanksgiving and help the City of Woodstock usher in the official start to the holiday season.
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Small Business Saturday November 25

Shop local and win big! Join Joe Cicero from STAR 105.5’s Morning Show on square from 10am-12pm. Learn more >

Horse-Drawn Carriage Rides
Select Dates: November 25-December 23

Historic buildings, brick-paved streets and tens-of-thousands of lights will transport you to a holiday movie scene.
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Annual Christmas Parade
November 26 at 2:00 pm

Come out and welcome Santa, plus all your favorite local organizations and businesses parading on floats!
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Cookies & Churros with Santa
November 26 from 2:30 - 4:00 pm

Immediately after the Annual Christmas Parade, join us to warm up and enjoy Cookies and Churros with Santa and tell him what you want for Christmas. Learn more >

Ladies Night Out
November 30 from 4:00 - 9:00 pm

Shop and sip your way around the Square. Enjoy laughs, make memories and get your holiday shopping kicked into high gear.
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Groundhogs Day
February 1 - 4, 2024

The film Groundhogs Day was filmed in Woodstock, IL in 1992 and the city gathers each year to celebrate and awaken the groundhog to find out if he sees his shadow or won’t he? Learn more >