Unwrap the festive magic of Woodstock with our detailed event guide. From long-time residents to new arrivals, our guide reveals the festive wonders of Woodstock.
Popular events this holiday season include the delightful Cookies & Churros with Santa, where families can enjoy sweet treats while sharing their wishes with Santa himself. The enchanting Christmas Tree Walk transforms the town into a winter wonderland, showcasing beautifully decorated trees that capture the spirit of the season. And the Horse-Drawn Carriage Rides are something you definitely don't want to miss, providing a charming way to experience the sights and sounds of Woodstock during Christmas. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Woodstock
- Cookies & Churros with Santa
- Christmas Tree Walk
- Horse-Drawn Carriage Rides
- White Christmas the Musical
- The Nutcracker Ballet
- Ladies Night Out
- Gingerbread Houses (Bannockburn)
See these and even more events listed below!
Woodstock Holiday Light Displays
Christmas Tree Walk
What to Expect:
Decorated tree display at the Woodstock Opera House.
Description:
The Christmas Tree Walk at the Woodstock Opera House features a beautifully decorated tree display from November 24 to December 31, offering a serene and festive atmosphere.
Where: Woodstock | More Info: Christmas Tree Walk
Horse-Drawn Carriage Rides
What to Expect:
Historic horse-drawn carriage rides through beautifully lit streets.
Description:
Take a leisurely ride through historic Woodstock's brick-paved streets and enjoy the tens-of-thousands of lights illuminating the festive atmosphere.
Where: Woodstock | More Info: Horse-Drawn Carriage Rides
Woodstock Holiday Markets and Shopping
Ladies Night Out
What to Expect:
Complimentary tote bags and local deals.
Description:
Join us for Woodstock's annual Ladies Night Out tradition, where you can shop and sip your way around the festively-lit Woodstock Square with your favorite friends and family. Enjoy seasonal music, live performances, and local deals. This delightful evening will feature a complimentary tote bag and coupon book, along with the famous Ladies Night Out lidded cup.
Where: Woodstock | More Info: Ladies Night Out
Woodstock Holiday Shows and Entertainment
White Christmas the Musical
What to Expect:
Classic holiday musical with Irving Berlin's iconic songs.
Description:
White Christmas the Musical is a classic holiday production featuring Irving Berlin's timeless songs and a heartwarming story of love and friendship.
Where: Woodstock | More Info: White Christmas the Musical
The Nutcracker Ballet
What to Expect:
World-class ballet performance with elaborate sets and costumes.
Description:
The Nutcracker Ballet, presented by Judith Svalander Ballet School, brings Tchaikovsky's world-renowned music to life on the Woodstock Opera House stage. Witness Clara's journey through a realm of fantasy with the school's talented ballet company.
Where: Woodstock | More Info: The Nutcracker Ballet
Woodstock Other Holiday Activities
Cookies & Churros with Santa
What to Expect:
Free cookies and churros with Santa.
Description:
Join the Woodstock Area Chamber of Commerce and Industry for a free event featuring cookies, churros, and Santa. Enjoy this festive gathering immediately after the Annual Woodstock Christmas Parade.
Where: Woodstock | More Info: Cookies & Churros with Santa
Gingerbread Houses
What to Expect:
Custom gingerbread house decorating with endless supplies and hot chocolate.
Description:
Celebrate the holiday season with your child by designing and decorating your very own gingerbread house. Our experienced instructors will guide you through every step, ensuring a fun and memorable experience for all.
Where: Bannockburn | More Info: Gingerbread Houses
Festive Fun in Nearby Cities!
Discover Holiday events in hundreds of cities worldwide. Check out these nearby locations for more festive fun!
- Crystal Lake (8 miles)
- McHenry (9 miles)
- Huntley (10 miles)
- Lake in the Hills (11 miles)
- Algonquin (13 miles)
- Carpentersville (17 miles)
- Round Lake Beach (19 miles)
- Belvidere (21 miles)
- Grayslake (21 miles)
- Elgin (21 miles)
- Mundelein (23 miles)
- South Elgin (24 miles)
- Streamwood (24 miles)
- Vernon Hills (25 miles)
- Libertyville (25 miles)
- Palatine (25 miles)
- Bartlett (26 miles)
- Wasco (26 miles)
- Hoffman Estates (27 miles)
- Hanover Park (27 miles)
- Rolling Meadows (27 miles)
- Buffalo Grove (27 miles)
- Gurnee (28 miles)
- St. Charles (29 miles)
- Wheeling (29 miles)
- Roselle (30 miles)
- Machesney Park (30 miles)
- Geneva (30 miles)
- DeKalb (31 miles)
- Pleasant Prairie (31 miles)
- North Chicago (31 miles)
- Bloomingdale (31 miles)
- Loves Park (31 miles)
- Mount Prospect (31 miles)
- Carol Stream (32 miles)
- West Chicago (32 miles)
- Elk Grove Village (33 miles)
- Beloit (33 miles)
- Zion (33 miles)
- Batavia (33 miles)
- Rockford (33 miles)
- Glendale Heights (34 miles)
- Northbrook (34 miles)
- Highland Park (34 miles)
- Des Plaines (35 miles)
- Addison (35 miles)
- Wheaton (36 miles)
- Glen Ellyn (36 miles)
- Kenosha (37 miles)
- Park Ridge (38 miles)
- Lombard (38 miles)
- Villa Park (38 miles)
- Glenview (38 miles)
- Janesville (39 miles)
- Elmhurst (39 miles)
- Aurora (39 miles)
- Niles (39 miles)
- Morton Grove (39 miles)
- Naperville (40 miles)
- Mount Pleasant (40 miles)
- Lisle (40 miles)
- Wilmette (41 miles)
- Skokie (41 miles)
- Downers Grove (42 miles)
- Melrose Park (42 miles)
- Portage Park (43 miles)
- Maywood (43 miles)
- Caledonia (43 miles)
- Westmont (43 miles)
- Belmont Cragin (44 miles)
- Muskego (44 miles)
- Oswego (44 miles)
- Albany Park (44 miles)
- Irving Park (44 miles)
- Woodridge (44 miles)
- West Ridge (44 miles)
- Franklin (45 miles)