Waupun's Winter Wonderland 

A City wide Kickoff to Christmas Celebration

In Lieu of Avenue of Angels, the whole city of Waupun is teaming up to provide a new way of ringing in the Christmas Spirit!

Save the DATES: Thursday, November 19th - Saturday, November 21st!

Thursday November 19th:

5:30pm and 7:30pm: Showing of the movie "ELF" in the west end parking lot (between Tractor Supply and Ace Hardware)

10am - 7pm:  Shopping hours extended during our Ho Ho Holiday Hours. Sign up by emailing Casey at info@waupunchamber.com.

Virtual Sign up:​


FESTIVAL OF LIGHTS (deadline for decoration) - Decorate your business to be entered to win sponsorships and Chamber Gift Certificates!

Friday November 20th:  

4pm-6pm: Santa in the Downtown green area (next to CJ Rock shop)

6:30pm: Holiday Parade - Sign your business, organization or entity up!

7:30- 9:30pm: Live Music by Shawna Starbird and Jason Braun  in the Downtown green area (next to CJ Rock shop)

Saturday, November 21st:

10am -12pm: Performance by "Just for Kix" Dance studio in the Downtown green area (next to CJ Rock Shop)

10am-12pm: Santa in the Downtown green area (next to CJ Rock Shop)

12pm - 2pm: Live Music by Shawna Starbird and Jason Braun in the Downtown green area

10pm-2pm: Treat station throughout Downtown. 

Help us spread the word - Facebook Event

Becoming a Sponsor for this WEEKEND LONG event! 

2020 Parade Information 

Calling all non-profits, businesses and organizations in the Greater Waupun Area! It’s time to secure your FREE spot in the first ever Waupun’s Winter Wonderland parade.


Parade Date: Friday, Nov. 20, 2020

  • Line Up at 5:45 p.m. in the St. Joseph Church Parking Lot (118 W. Main St)

  • Parade starts at 6:30 p.m.


Parade Route:

St. Joseph’s church, east on Main Street through Downtown, turning north on Fond du Lac Street, ending at the intersection of Fond du Lac Street & Franklin St.



  • Please ensure your float is family-friendly and holiday-themed.

  • Lights & music are encouraged! Be creative!

  • NO Santa entries will be allowed as the Chamber provides a Santa for the parade.

  • NO throwing candy. You may walk on the side of the street and hand items out but NO throwing. This is a safety issue. Thank you.

  • NO cost to enter!

  • Prizes awarded:

    • First place: $100 Chamber Gift Certificate

    • Second place: $50 Chamber Gift Certificate

    • Third place: $25 Chamber Gift Certificates


Festival of Lights Information

Want to promote your business in a fun way? Looking to spread some holiday cheer? Join the 2020 Festival of Lights – the City of Waupun, Waupun Downtown Promotions, and Waupun Area Chamber of Commerce, first ever business - decorating contest hosted during Waupun’s Winter Wonderland. Your business will be on display during the weekend -long event hosted throughout the City of Waupun. Waupun Winter’s Wonderland patrons visit Santa, participate family fun activities, enjoy holiday music festive parade, and vote on their favorite decorated business/organization!


Festival of Light Set Up:

  • BEFORE Wednesday, November 18th


Festival of Light Display:

  • Thursday, November 19th – December 25th


Festival of Light Take Down:

  • Anytime After December 25th



  • FREE to enter!

  • Each business/organization must supply their own lights, garland, power cords, decorations, etc.

  • Each business/organization must provide the location of their decorations

    • Ie – Waupun Figure Skaters are decorating Waupun Community Center

  • Prizes awarded:

    • First place: DRIVING RANGE sponsorship at 2021 Chamber Golf Outing (value of $350) & $100 Chamber Gift Certificate

    • Second place: HOLE CONTEST sponsorship at 2021 Chamber Golf Outing (value of $200) & $50 Chamber Gift Certificate

    • Third place: HOLE sponsorship at 2021 Chamber Golf Outing (value of $100) & $25 Chamber Gift Certificate

  • Please keep safety in mind when decorating.

  • The Waupun Downtown Promotions, Waupun Area Chamber of Commerce & City of Waupun are NOT responsible for lost, damaged or stolen items from participating businesses or organization.


Become a 2020 Sponsors!

Wonderland Sponsor:

"Your Business Name and logo Here"

Movie Sponsor:

National Exchange Bank and Trust

Live Music Sponsor:

Real Sportscards

Santa Sponsor:

BJ DeMaa and Friends at City of Waupun 

Angel Sponsor:

Bentz Automotive

Tom Dooley's Apple Orchard

My Property Shoppe

SIA Insurance

Prairie Groove Orthodontics 

Tom Dooley's Apple Orchard

Waupun Fine Arts