Artistic rendering – Event may differ
Winter in Woodstock Events
Woodstock transforms into a winter wonderland, offering a magical holiday experience for all. From the festive Lighting of the Square to charming horse-drawn carriage rides and a lively New Year's Eve Bash, the town buzzes with seasonal spirit. Enjoy unique shopping, delightful performances like 'The Nutcracker Ballet' and holiday concerts, and family-friendly events including Santa visits and workshops. Discover why Woodstock is a celebrated 'Merriest Main Street'!
What to Expect
Historic 'Merriest Main Street' with diverse holiday events.
Know Before You Go
- Tickets: $$
- Pets: No pets allowed
Other Christmas Events Near Woodstock
Local Insight & Ratings
Family Friendly
Best For
Families, couples, holiday shoppers
Vibe
Festive, charming, community-oriented
Energy Level
Moderate
Budget
$$
Photo Friendly
Weather Sensitivity
Moderate
Special Events & Promotions
- Lighting of the Square
- Small Business Saturday
- Annual Christmas Parade
- Cookies & Churros with Santa
- Ladies Night Out
- Horse-Drawn Carriage Rides
- New Year's Eve Bash
- Groundhog Days Celebration
- Shop. Dine. Save. Win! promotion
- Christmas Tree Walk
- Gingerbread Walk
Location
Event Details
Duration
Multiple events throughout the season
Ages
All ages
Neighborhood
Woodstock Square Historic District
Timed Entry
No
Featured Performers
- Felix and Fingers Dueling Pianos
- Axiom Brass
- The Four C Notes
- Ed Hall
Organizer
Real Woodstock
Food & Drink
Food trucks, restaurants, and beverage vendors available.
Quick Actions
Tips & Advice
- Check the Metra schedule for convenient train travel from Chicago to avoid parking hassles.
- Many events are clustered around the historic Square, making it easy to walk between activities.
- Book tickets for Opera House shows and the New Year's Eve Bash in advance, as popular events sell out.
- Dress in layers for outdoor events like the Lighting of the Square and the Christmas Parade, as weather can be unpredictable.
- Take advantage of the 'Shop. Dine. Save. Win!' promotion to support local businesses and get rewarded.
Frequently Asked Questions
What is the main attraction of Woodstock during the holidays?
Woodstock is celebrated as one of America's 'Merriest Main Streets', offering a wide array of festive events, charming decorations, and a strong sense of community holiday spirit.
Are there specific events for children?
Yes, there are several family-friendly activities, including Cookies & Churros with Santa, a Noon Year's Eve celebration, and the Christmas Parade.
What kind of shopping can I expect?
You can find unique gifts and artisanal products at various markets, including Small Business Saturday and the Tinsel and Treasures Market, alongside local boutiques.
Is there live entertainment available?
Absolutely! The Woodstock Opera House hosts a variety of performances, including theater, holiday concerts, and ballet like 'The Nutcracker'.
How can I get to Woodstock?
Woodstock is accessible by car via I-90/94W and IL-47, or conveniently by the Metra Union Pacific/Northwest Line from downtown Chicago.
Always check the official website for the most current information.
We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly.