Scene I
Tue, Dec. 1
Tree Lighting & Drive-In Movie
Watch downtown light up for the season, then settle in for a holiday drive-in movie.
Once upon a time in Waupun…
Once Upon a Christmas
December 1 to 5, 2026
Five days of holiday magic downtown, from the tree lighting and a drive-in movie to live reindeer, date night, the Christmas parade and the Sugar Plum Stroll.
See the scenesEvents calendar
Tonight’s program
Five scenes of Christmas magic
Times and details for each night coming soon.
Scene II
Wed, Dec. 2
Winter Market & Live Reindeer
Say hello to real, live reindeer and shop the winter market, open Wednesday and Thursday.
Scene III
Thu, Dec. 3
Date Night Downtown
Horse rides, a night out on the town and more surprises to be announced.
Scene IV
Fri, Dec. 4
Parade & After Party
Cheer on the Christmas parade, then party on at Jud’s.
Scene V
Sat, Dec. 5
Sugar Plum Stroll
Sip warm drinks and try tasty bites while you shop Waupun.
Scene III · Thu, Dec. 3
A night to remember
Date night, Waupun style.
Snowy streets, twinkling lights and someone special. Here’s everything you need for a night out, just around the corner.
- Horse-drawn carriagesBundle up for a carriage ride through snowy, twinkling downtown.
- DineLinger over dinner and a festive drink at a hometown favorite.
- ShopBrowse the outdoor Christmas Market (open Wednesday and Thursday) and downtown shops for something special.
- Gift-wrap stationDrop off your finds and let them be wrapped and ready to give.
- Explore the artsStroll past sculptures and local art that tell Waupun’s story.
- Get outsideWalk a winter trail or wander a snowy park together.
More date night surprises will be announced soon!
A winter’s tale
Picture the season in Waupun.
Photos from holiday shopping and past winter events in Waupun.
The story starts early