Chilly Willy Winter Run Series - Great Gobble Wobble 5K and 10K

Thursday, Nov 26, 2020 at 8:00am

Roosevelt Park
630 South Main Street
Oconomowoc, WI 53066

Please call before attending any community events. It is likely that they will be postponed or canceled as a result of the coronavirus. You can find CDC coronavirus information at; AARP has additional resources at

Join us for a fun filled 5K on turkey day either local or virtual. The average American consumes 4,500 calories on turkey day. We can help you burn off some of those calories before your tryptophan induced nap. Here is a simple calculator to determine how much time you need to run to burn off 4,500 calories.

Race Times

We originally set the race to have multiple times because of the participant caps. The county has lifted those caps and then reinstated them at a higher level. Depending on the attendance, we might combine the times. If the race becomes as large as last year we will add additional times. Register for your preferred time, but know that it might be changed. 

Chilly Willy Winter Run Series

We have permitted three races for the series including the Gobble Wobble. If/when we release a series registration and you want to sign up for it, let us know and we will credit your series registration with the cost of this race.

THE Miler 5K

Why not make it a double? Run the Oconomowoc Gobble Wobble on Thursday and then THE Miler 5K on Friday!


Can't make it to Oconomowoc? No worries, run it virtual and we will send you your shirt and medal. Download the RaceJoy app and it will automatically upload your results!


This might be the flattest course in Wisconsin.  The course starts at Roosevelt for a super fast out and back along the Lake Country Trail (paved). At the turn, the elevation is a whopping 20 feet higher than the start. Make the turn and it's all "downhill" from there.

Course Map 5K

We will continue with our social distancing plan until further notice. Winter complicates things because this is Wisconsin and it’s cold! 

For the winter races, we will have packet pickup at our office prior to the event day. We strongly encourage you to pick up your packet prior to race day or have someone pick it up for you. On race day, packet pickup will be available, but it will be outside. We will not have any buildings open to the public, unless the current restrictions are lifted. 

Race Format

The 10’ socially distanced staggered start will continue. We will extend the start times to allow people to stay warm in their cars as long as possible. We recommend you select a start cone a few minutes before the race is scheduled to start. If you would rather stay in your car until the race has started and then head to the start line, that is perfectly acceptable, too. We ask that you maintain the 10’ social distancing as outlined in our plan. The start line will stay open for 15 minutes past the scheduled start time.

We are hopeful that we will be able to reduce the distancing requirements as we get closer to a vaccine. However, it would not be wise at this point to jam 250 people in a small building. We don’t particularly like this process either, but it is what we have to do to keep everyone safe and to keep permits so we don’t have to go back to virtual races.


Top 3 male & female finishers in 5 year age groups will receive a custom medal.

Cost and Time:

5K - $35

8:00AM CST - 9:00AM CST

Price increases after November 25, 2020 at 11:59pm CST

5K - $35

9:00AM CST - 10:00AM CST

Price increases after November 25, 2020 at 11:59pm CST

10K - $37.50

8:00AM CST - 11:00AM CST

Price increases after November 25, 2020 at 11:59pm CST

Virtual 5K - $30

Registration ends November 26, 2020 at 11:59am CST

10K Virtual - $30

Registration ends November 26, 2020 at 11:59am CST

Click Here to Register

This event listing provided for the Oconomowoc community events calendar. Community events are not associated with or sponsored by AARP, but may be of interest to you. If you have an event to share, let us know!

Images provided by, Ticketmaster

More from AARP in Oconomowoc

Upcoming AARP Events

View All AARP Events »

You can find CDC’s latest coronavirus information at; AARP information and resources are at En español, visite

AARP Member Card

Join or Renew Today


  • Immediate access to your member benefits
  • Discounts on travel and everyday savings
  • Subscription to the award-winning AARP The Magazine
  • An ally on the issues that matter most to you in Oconomowoc
  • Free membership for your spouse or partner