The Cycle Caledon Challenge (CCC) is a bike tour for the cycling enthusiast. Starting and ending at the Caledon Ski Club West Lodge situated on the Niagara Escarpment, tour routes of 40 kms, 60 kms, 100 kms (metric century), and 160 kms (100 miler) will challenge cyclists with the rolling terrain of the Hills and Headwaters of the region.

The 40 km route travels on Winston Churchill Boulevard and returns along Shaws Creek Road. It’s the same Winston Churchill Boulevard that stretches from Mississauga but the scenery is quite a bit different with trees lining both sides of the road and a crossing over a single land bridge.

The 60 km route starts where the 40 kms route ends and forms the second leg of the 100 km route. This loop starts with a descent to the base of the Caledon Ski Hill then slowly ascends back up to the historic village of Alton. From Alton the route travels to the border of Orangeville then returns south through Caledon Village. After a long rolling descent cyclists must climb back to the starting point to cap off the 100 kms.

The 160 km/100 mi route, completes the 100 km route and heads out for a final 60 km loop. There is a long descent towards the village of Terra Cotta and some flat lands before the final challenge. After the final rest stop in the village of Inglewood comes the last set of challenging climbs. There is a short and flat 1.5 km section of packed dirt road connecting with the infamous Forks of the Credit road. Here starts the final switch back ascent to complete the tour and return riders to the Caledon Ski Club.