Artistic rendering – Event may differ
Woodstock's Winter Wonderland Events
Experience the enchanting 'Winter in Woodstock' season, a town recognized for its festive spirit. From the dazzling Lighting of the Square to the beloved Christmas Parade and unique shopping events, there's a magical holiday atmosphere for everyone. Enjoy live entertainment, charming carriage rides, and festive activities that capture the heart of the season.
What to Expect
Historic town square transformed into a festive holiday destination.
Know Before You Go
- Tickets: $$ – Get tickets
- Parking: Parking information is available on the website.
- Pets: No pets allowed
Other Christmas Events Near Woodstock
Local Insight & Ratings
Family Friendly
Best For
Families, couples, holiday shoppers
Vibe
Festive, charming, historic, community-oriented
Energy Level
Moderate
Budget
$$
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
Varies by event
Ages
All ages
Neighborhood
Historic Square
Timed Entry
No
Featured Performers
- Axiom Brass
- The Four C Notes
- Felix and Fingers Dueling Pianos
Organizer
Real Woodstock
Food & Drink
Food and drinks available from local vendors and restaurants.
Quick Actions
Tips & Advice
- Check the Metra schedule in advance for train times to Woodstock to avoid parking hassles.
- Arrive early for popular events like the Lighting of the Square and the Christmas Parade to secure a good viewing spot.
- Wear comfortable shoes as many events involve walking around the historic Square and exploring shops.
- Book tickets for Opera House shows in advance, as popular performances like 'The Nutcracker Ballet' tend to sell out.
- Take advantage of the 'Shop. Dine. Save. Win!' promotion to get rewarded for supporting local businesses.
Frequently Asked Questions
What is the main attraction during the holiday season in Woodstock?
Woodstock's historic Square is the heart of the holiday festivities, featuring events like the Lighting of the Square, a Christmas Parade, and numerous shops and dining options.
Are there specific events for children?
Yes, there are several family-friendly activities, including Cookies & Churros with Santa, horse-drawn carriage rides, and various performances at the Opera House.
How can I get to Woodstock for the events?
Woodstock is accessible by Metra train from Chicago or by car via I-90/94W and IL-47.
Where can I find a full schedule of events?
A comprehensive calendar of events is available on the Real Woodstock website.
Is there a cost associated with attending the holiday events?
While many events are free to attend, some performances and specific activities may require tickets or have associated costs.
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.