Milwaukee Area Winter Fun Runs and 5Ks


winter run

Running? Outside?? In winter??? IN WISCONSIN?!?!

Yep! Time to grab your running shoes, get outside, and get those endorphins pumping. Put on your most festive holiday outfit and have fun running, walking, or trotting!

Many runs are in person this year, but due to COVID restrictions and safety issues, most offer a virtual option, as well. The great part about that is you can run from anywhere!

Please check sites for updates and/or virtual options closer to the race date for those races still scheduled in person.

The team at Milwaukee Mom is working hard to remain your go-to spot for parenting resources in the Greater Milwaukee Area. While we will do our best to be as up-to-date as possible, please be aware that we are still dealing with changes related to the COVID-19 Pandemic. Please consult your local public health authority for social distancing recommendations and call ahead to confirm the hours and offerings of any business or organization listed.

Milwaukee Area Winter Fun Runs and 5Ks


Milwaukee Turkey Trot – November 25th

  •  Run this 8K, 5K or Kid’s Dash in person this year. Registration is currently open until the day of the race. Virtual options available as well.

Drumstick Dash – November 25th 8:30 am start time

  • Participate by running or walking in person a 5K or a 2.5K. Virtual option available too. Proceeds benefit Feeding America Eastern Wisconsin.


Waukesha Santa 5k Run & Walk – December 5th

  • Jingle your bells at this race and run or walk a 5K through downtown Waukesha. Virtual option for both adults and students.

Santa Cycle Rampage – December 5th all-day

  • Prefer to bike instead of run? Dress as Santa and enjoy a ride when and where you feel safe. There will not be any workers or streets closed for a route this year due to COVID. Registration is free, but please consider purchasing custom-made merchandise to support the race.

Santa Hustle – All of December

  • 3.1 miles, 6.2 miles, 13.1 miles, or even 26.2 miles at your choice of location, any duration of time, during the designated dates of December 1 – 31, 2020. Run by yourself or with a group. Just get out and have a fun time!

Festivus One-Miler – TBA

  • This event is will not be taking place live this year. Watch the site for more details when and if a virtual option is available.

Cedarburg Santa Dash Away 5K – December 11th

  • Run or walk a 5K starting at W63N641 Washington Avenue, Downtown Cedarburg. Free Christmas sweater t-shirt and Santa mask if you register by November 19th.


Waukesha Janboree Frosty 5K – January 23rd

  • Enjoy the annual Janboree festival and get some free hot cocoa at the end! The race begins and ends at Frame Park.

Samson Stomp & Romp – TBA

  • Please watch the site for updates on this fun and family-friendly event at the Milwaukee County Zoo.

Throughout the Season

Winter Run Series – Multiple Dates

  • You can still sign up for the remaining races: The Big Chill, Run into the New Year, Cupid Shuffle, and Luck of the Irish!

Chilly Willy Run Series – November 6th through March 27, 2022

  • You can sign up for all or part of this 8 race series that goes on from November to March!

Are you and your family going to run run like Rudolph and the other reindeer? If so, drop a comment below to let us know which race(s) you’ll be running! If we’ve missed any, make sure to let us know so we can add them to our list!


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