Described as the best cycling in the Midwest, and possibly the most challenging, the Ten Thousand offers tons of gravel, relentless rolling hills, and more cows than you’ve ever seen. Don’t take our word for it: here’s a clip of the Gravel Cyclist on a recent course.

100 / 80 / 40 mile routes. Presented by Black Saddle Bike Shop, Comrade Cycles, Driftless Cycling Tours, and numerous volunteers.