What to Expect This Christmas in Woodstock!
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!
Find the best Christmas events in Woodstock this year!
Top Christmas Events In and Around Woodstock
- Annual Woodstock Christmas Parade
- Cookies and Churros with Santa
- Woodstock Christmas Tree Walk
- Conifera Tree Farm Christmas Tree Selection (Harvard)
- The Nutcracker Ballet
- Woodstock Ladies Night Out
- Elgin Symphony Orchestra Holiday Concert (Crystal Lake)
- A Very Merry Huntley (Huntley)
- Grand Geneva's Christmas in the Country (Lake Geneva)
- Santa's Village Magical Christmas Drive-Thru Experience (East Dundee)
🎃 Explore all 10+ featured events below!
Woodstock Christmas Events
Woodstock Christmas Markets and Shopping (2)
When
Sunday, November 23, 2025
Event Details
Event Description
Experience the joy of selecting the perfect real Christmas tree at Conifera Tree Farm. They offer a delightful choose-and-cut experience with a variety of spruce, fir, and pine trees, alongside premium pre-cut options from Wisconsin. Visitors can also find beautifully crafted wreaths and garlands made fresh on-site, adding a festive touch to their holiday celebrations.
More
When
Thursday, December 4, 2025
Event Details
Event Description
Get ready for a festive evening at Woodstock's Ladies Night Out! This popular event returns with a new theme, offering a perfect opportunity to shop, dine, and celebrate with friends. Attendees will receive a complimentary tote bag and a coupon book packed with local deals. Don't miss this chance for a memorable night out in Woodstock.
MoreWoodstock Christmas Food, Drink and Parties (1)
When
Sunday, November 30, 2025
Event Details
Event Description
Immediately following the Annual Woodstock Christmas Parade, families can head to the Historic Woodstock Square for a delightful 'Cookies and Churros with Santa' event. This festive gathering offers children a perfect opportunity to share their Christmas wishes with Santa, indulge in sweet treats, and embrace the holiday spirit.
MoreWoodstock Christmas Movies, Theater and Entertainment (1)
Event Details
Event Description
Experience the timeless magic of The Nutcracker Ballet, a beloved holiday tradition. This enchanting performance brings Tchaikovsky's iconic score to life with stunning choreography and captivating artistry. Join Clara on her whimsical journey through a world of brave toy soldiers, mischievous mice, and the dazzling Sugar Plum Fairy. A perfect festive outing for the whole family.
MoreWoodstock Other Christmas Activities (2)
When
Sunday, November 30, 2025
Event Details
Event Description
Join the festive kickoff to the holiday season at Woodstock's Annual Christmas Parade. This beloved event features a vibrant procession of local organizations and businesses showcasing their creativity on decorated floats. The highlight of the parade is the arrival of Santa and Mrs. Claus, bringing holiday cheer to all.
More
When
Sunday, November 24, 2024
Event Details
Event Description
Stroll through the enchanting Christmas Tree Walk, a delightful holiday tradition featuring a captivating display of uniquely decorated trees. Located at the historic Woodstock Opera House, this event transforms the venue into a festive wonderland, perfect for soaking in the holiday spirit.
MoreNear Woodstock
Crystal Lake Christmas Events
Mchenry Christmas Events
Huntley Christmas Events
Lake In The Hills Christmas Events
Algonquin Christmas Events
Carpentersville Christmas Events
Round Lake Beach Christmas Events
Belvidere Christmas Events
Grayslake Christmas Events
Elgin Christmas Events
View Our Interactive Map for More Events Around Woodstock
Discover thousands of christmas events across the country
Explore Other Cities
Find events in different locations
Our Process
With 20 years of experience, we use AI technology to build the most comprehensive list of christmas events events.
Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.
Learn More About Our Process