Winterfest/Cookie Walk
Visitors can stroll through downtown businesses collecting cookies, chocolates, and treats using a special event tin and map. The event features live carolers, choir and saxophone music, storytelling, and an appearance by Santa, alongside a screening of The Polar Express at Lake Theatre. Guests can also enjoy complimentary hot cocoa and write letters to Santa.
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Plan Your Visit
Website / Tickets
When
Hours
Winterfest: 10:00 am–3:00 pm; Cookie Walk: 11am–3pm; pre-purchased tin pickup: 10 AM–2 PM.
Ages
All ages
Neighborhood
Downtown Oak Park
Food & Drink
With a pre-purchased tin and map, visitors can collect cookies, chocolates, and treats from participating businesses; complimentary hot cocoa is also served.
Parking
Free metered/Pay-By-Plate parking (2 Hours Max) and free garage parking (Holley Court Garage and Lake/Forest Garage) the Friday after Thanksgiving and every Saturday from November 30th through December 21st. Garage parking is always free on Sunday. Metered/Pay-By-Plate is always free after 8pm on weeknights and all day Sunday.
Going?
Location
Tips & Advice
- Bring your confirmation email and State ID when collecting a pre-purchased Cookie Walk tin and map.
- Pick up the tin at the Hospitality tent in Lot #3 on Marion Street before setting out to collect treats.
- Order no more than one tin per household, as multiple orders are not allowed.
- Dress for the weather because the Cookie Walk proceeds rain or shine.
- Use the free Saturday garage parking or the free Sunday parking options if they fit your visit.
Special Events & Promotions
- The Cookie Walk requires a 2026 Cookie Walk tin to collect treats from participating businesses.
- Santa appears at Winterfest on December 5.
- The Polar Express is shown as a free holiday movie on December 5.
- Free metered parking and garage parking are offered on the event Saturday.
Links & Contact
Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.
Frequently Asked Questions
What does the Cookie Walk include?
With a 2026 Cookie Walk tin and map, visitors can collect cookies, chocolates, and treats from participating downtown businesses.
Do I need to buy a tin to join the other Winterfest activities?
The tin is required to collect Cookie Walk treats; the event information does not state that it is required for the other activities.
Where do I collect a pre-purchased Cookie Walk tin?
Pick it up with the map at the Hospitality tent in Lot #3 on Marion Street, bringing your confirmation email and State ID.
What entertainment and activities are offered?
Winterfest includes live carolers, choir and saxophone music, storytelling, Santa, letters to Santa, complimentary hot cocoa, and a free screening of The Polar Express at Lake Theatre.
What happens if it rains or snows?
The Cookie Walk takes place rain or shine.
Browse Christmas in Oak Park
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. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.