Winterfest & Cookie Walk

About this event

Winterfest in Downtown Oak Park

Join us at Winterfest on Saturday, December 5 for a celebration of the holiday season in Downtown Oak Park! Check out all the details below and mark your calendars for a day full of festive fun and community cheer.

11am–3pm – Cookie Walk

The Cookie Walk begins as participating Downtown Oak Park businesses hand out cookies, chocolates, and sweet surprises to those with a 2026 Cookie Walk tin.

Free Hot Cocoa & Letters to Santa!

Warm up with complimentary hot cocoa generously provided by Wise Cup and served by the Collaboration for Early Childhood! Kids can also write their letters to Santa while enjoying the holiday festivities.

Winterfest Entertainment – Saturday, December 5

• Free Holiday Movie (The Polar Express) – Lake Theatre, 10:00 AM

• Heritage Chorale – 10:00–11:00 AM

• Santa – 11:00 AM–2:00 PM

• Canterbury Carolers – 11:30 AM–1:30 PM

• OPRF Show Choir – 12:00 PM

• Grace Church Carolers – 12:30–2:00 PM

• Winter Tales from Around the World at The Book Loft (Storytellers from Actor’s Garden) – 12:00–2:00 PM

• Holiday Saxophonist – 12:00–2:00 PM

The Cookie Walk features cookies, chocolates, & treats from…

… and many more!

PLEASE NOTE BEFORE PURCHASING:

• ONE TIN ORDER LIMIT PER HOUSEHOLD – let your neighbors get in on the fun too!

• PICK UP your pre-purchased cookie tin along with a map to collect your cookies, chocolates, and treats at participating businesses.

• When: Sat, December 5th from 10 AM – 2 PM (the cookie walk is held 11 AM – 3 PM)

• Where: Hospitality tent located in Lot #3 on Marion Street between Q-BBQ (124 Marion) & Cold Stone Creamery (134 Marion)

• Bring: Confirmation email & State ID

• There will be no refunds.

• The cookie walk is held snow, rain or shine.

ONE TIN ORDER LIMIT PER HOUSEHOLD – PLEASE DO NOT MAKE MULTIPLE ORDERS.

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Free Holiday 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.

For questions, please contact The Village of Oak Park Parking & Vehicle Services at parking@oak-park.us or 708-358-PARK (7275).

View the Parking Map

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