Additional Information
Parking Information
Parking is available on-site. However, with over 2,000 participants expected, we strongly encourage carpooling to help reduce congestion and ensure everyone has a smooth arrival.
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Awards, Awards & More Awards
Overall Awards
The top overall male and female runners in each distance will receive a custom award provided by our partner, Ridgeway Woodworks.
Age Group Awards
The top 3 male and female finishers in 5-year age groups will receive a custom woodle. Age groups start at 0-14, then continue in 5-year increments.
Finisher Woodles
Every participant will receive a magnet woodle crafted by Ridgeway Woodworks as a special keepsake.
The Average Joe & Jane Awards
Not everyone can be first, but someone has to land right in the middle—and we celebrate that! The Average Joe & Jane Awards are presented to the male and female runners who finish exactly in the middle of all registered participants. More about the Average Joe & Jane awards.
Miss Your Award?
If you missed picking up your award, here’s how to get it.
Celebrate your achievement.
Day of Registration
We highly recommend registering in advance—it’s quick and can be done from your phone!
If you choose to register on race day, you must register electronically; paper registration is not available.
See you on race day!
Volunteer Opportunities
We’re looking for enthusiastic volunteers to help with everything from aid station support to course marshaling. Your assistance makes these events possible, and we’d greatly appreciate your help!
Volunteer Perks:
All volunteers will receive a free entry to a future race as a thank-you for their time and support.
How to Volunteer:
- Click the Volunteer link in the menu above to sign up.
- For more details on volunteering, click here.
Join us in creating an amazing event experience for everyone!

Charity Partner
The Silver Circle Foundation, Inc., a 501(c)(3) nonprofit organization, is proud to support our firefighters, police officers, veterans, and troops serving overseas.
Through charitable giving, care packages, and fundraising efforts, we aim to provide much-needed assistance and show our gratitude for their service and sacrifice.
Your participation helps make a difference—thank you for supporting this important cause!

Partner with Us for Your Workplace Wellness Program!

Let us support your workplace wellness initiatives and make it easy to get your team involved.
How It Works:
- Reach Out: Share your workplace information with us.
- Custom Code: We'll create a unique discount code for your wellness members to use during registration. The code can waive or reduce the registration fee based on the discount your program offers.
- Post-Race Invoice: The day after the race, we’ll send you an invoice for the discounted registrations, which can be conveniently paid online.
It’s that simple! Let’s work together to promote health and wellness in your workplace.
Aid Stations
There will be one aid station on the 5K course. The 5K runners will pass the aid station twice. There will be two aid stations on the 10K course. The 10K runners will pass each of them twice.
Walkers Welcome!
Walkers are welcome to join any distance. Just select your desired distance when registering and check the course closure time to ensure you can finish before the course closes.
Although the Walk Division is timed, it’s not competitive, and there are no age group awards. However, walkers will still receive a finisher woodle.
Enjoy the trail and have a great race!
Insurance
We get it—life happens! That’s why we recommend purchasing event insurance during checkout.
What is RegShield Insurance?
Race insurance, provided by RegShield (a FanShield product), offers peace of mind by reimbursing the registration cost if you’re unable to attend due to covered reasons, including:
- Accident
- Illness
- Family emergency
Need Help with Insurance?
RegShield is a third-party provider. For any questions related to your plan, contact FanShield:
help@fanshield.com
1-844-849-4827 EXT.
This event is owned, produced, timed, and managed by Silver Circle Sports Events, LLC, a veteran-owned event management company based in Oconomowoc, Wisconsin.
Silver Circle Sports Events provides professional race management, chip timing, registration support, course logistics, equipment, marketing support, and race-day operations for running, walking, rucking, and multisport events throughout Wisconsin.
Planning an event of your own? Whether you are organizing a 5K, walk, fundraiser, corporate wellness event, or full race production, we can help bring it to life.
Need help with an event? Contact us HERE.
What is rucking?
Rucking is a physical activity that involves walking or hiking with a weighted backpack (called a rucksack). The term comes from the military, where soldiers train and operate carrying heavy loads over long distances. In civilian fitness and recreation, rucking is gaining popularity as a versatile and low-impact workout. We now offer it at all Chilly Willy Events!
More information about rucking.
Although the Ruck Divisions are timed, it’s not competitive, and there are no age group awards. However, ruckers will still receive a finisher woodle.
Average Joe & Jane Awards
The Average Joe & Jane Awards are back for the Chilly Willy Series 5K Runs and are presented to the male and female runner who finishes in the exact middle of all runners. Winners will receive a T-shirt and custom medal!
Dogs
We’re sorry, but dogs are not permitted on Oconomowoc school property. Please help us avoid any awkward conversations by leaving your furry friends at home. Thank you for understanding!
RaceJoy
Interactive Race Day Experience with RaceJoy
Live Phone Tracking, GPS Progress Alerts and Cheers!
We are providing you with RaceJoy as part of the official race experience for the Great Gobble Wobble.
Download the RaceJoy mobile app in advance to ensure proper phone setup. Invite your friends and family to track you and send you cheers!
