Thank You to all our participants of the 2026 Cheddar Challenge!
We can't wait to see you in 2027!
00
DaysDays
00
HrsHours
00
MinsMinutes
00
SecsSeconds
The Cheesiest Gravel Around
What is The Cheddar Challenge?
Ride along with the participants and see the different surfaces you will encounter if you decide to challenge yourself! Check out "Ride with Mike" on our gallery page.
Cheddar Challenge 2026 Start & Finish at XTREME SPORTSPLEX
Cash Prizes for the top 3 Over All Men & Women Xtra Sharp Cheddar 50 Miles
Xtra Sharp Cheddar 50 miles
1st Place Over All
2nd Place Over All
3rd Place Over All
&
Cash Prize Drawing
3 prizes for 3 random participants that finish
Thank you to the 2026 Sponsors of our Cash Prizes: CAM's Watertown Pizzeria
RocaFleet Watertown
Beller's Auto
Xtra Sharp Cheddar
50 miles - Ride surfaces include tarmac, smooth dirt, gravel, cobbles and double track. Gravel bike is recommended; a Mountain Bike is a viable option. Starts at 9:00am
Sharp Cheddar
31 miles - Ride surfaces include tarmac, smooth dirt, gravel, cobbles, and chip & seal. Gravel bikes are recommended; a Mountain Bike is a viable option. Start at 9:05am.
Mild Cheddar
10 miles - Ride surfaces include tarmac, smooth dirt, gravel, chunky rocks, and double track. A Gravel or Mountain Bike is recommended, and a Hybrid is a viable option. Start at 9:05am
ALL PARTICIPANTS RIDING BICYCES- A HELMET IS REQUIRED
Course Links**
Xtra Sharp Cheddar: https://ridewithgps.com/routes/48061772
Sharp Cheddar: https://ridewithgps.com/routes/48061902
Mild Cheddar: https://ridewithgps.com/routes/48061920
**Courses may be updated if required by road closures and or current unforeseen changes in road surfaces.
THE CHEDDAR CHEESE FESTIVAL
We are proud to partner with the Adams Cheddar Cheese Festival for a 3rd year!
Join us & enjoy all that the Adams Cheddar Cheese Festival has to offer after!
Refund Policy
Please note: All registration fees for the Cheddar Challenge are final and non-refundable. We incur significant upfront costs—including permitting, insurance, and participant materials—regardless of attendance. If you are unable to ride, we do offer the option to transfer your entry to another rider or defer your registration to next year's event.
Subscribe
Sign up to get event updates.