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Hilly Hundred 2021

We’re excited to announce the 7th Annual Hilly Hundred!

Free online registration at

Ready for the challenge of riding a FREE century, 66 miles or 32 miles in Brooksville? Not ready for the long rides, take the 32 mile route option! Same great scenery with some of the hills too.

FREE to participate, but we encourage all participants to donate a new, unwrapped toy or gently used bicycle to our toy drive for Guardian Ad Litem of Hernando County.

This is a SELF-SUPPORTED ride. The route does pass numerous convenience stores / parks which will serve as the supply points if you need anything. Please be mindful of COVID regulations and requirements that may still be in effect at convenience stores and parks. Cycling naturally socially distances riders while on the bike but please follow all suggested COVID guidance at the start and rest stops, socially distance and respect mask guidelines. By participating in this event, you recognize you are participating at your own risk for any potential COVID exposure. This is a drop ride but several pace groups will form based on attendance.

Rollout: 7:30 AM Sharp
Distance: 100 Miles
Elevation: 3,773 ft

Hilly Hundred Route:

Hilly 66 Route:

Hilly 32 Route:

You can upload GPS/GPX info after clicking on the route link above, then the top right corner offers “Export” option, which will have GPS/GPX info.

The Hernando County Sheriff’s Department will be getting us safely through town for the start of our ride. The rest of the route is open roads. Roads are very well marked.

Road Rules:

  • You agree that participating in this event you are RIDING AT YOUR OWN RISK
  • Safety is our #1 priority. Please use hand or verbal signals to alert cyclists of potential dangers. Your signals should always be obvious and clear.
  • Helmets are always required on all shop rides
  • Headphones or any ear device is not permitted on group shop rides

Register online at

Event Calendar

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