Winter in Woodstock

Experience the MAGIC!

Woodstock, voted one of the TODAY Show’s “Merriest Main Streets” in America, is ready to welcome residents and visitors alike!

From the Lighting of the Square on the Friday after Thanksgiving to our beloved Groundhog Days Celebration on February 2—and countless festive events and activities in between—there’s no better place to celebrate the season than right here in Woodstock!

Special Events

Lighting of the Square
Friday, November 28 at 4 - 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.
Learn more >

Small Business Saturday
Saturday, November 29

Shop small, shop local! This Small Business Saturday, explore Woodstock’s charming boutiques, specialty shops, and unique finds all around town. Every purchase supports the heart of our community.

Annual Christmas Parade
Sunday, November 30 at 2 PM

Come out and welcome Santa, plus all your favorite local organizations and businesses parading on floats!
Learn more >

Cookies & Churros with Santa
Sunday, November 30 at 2:30 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
Thursday, December 4

Shop and sip your way around the Square. Enjoy laughs, make memories and get your holiday shopping kicked into high gear.
Learn more >

Horse-Drawn Carriage Rides
December 7, 14 & 21

Historic buildings, brick-paved streets and tens-of-thousands of lights will transport you to a holiday movie scene.
Learn more >

New Year's Eve Bash with Felix and Fingers Dueling Pianos
December 31

Ring in the new year at the ultimate part at the Woodstock Opera House. An evening of music, dancing, food and a midnight champagne toast will start 2026 off on the right foot! Learn more >

Groundhog Days in Woodstock
January 30 - February 2

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 >