Madison has one of the most widespread bike trail systems and the largest population of bike owners in the United States—a bikers haven. The Kettle Moraine State Forest offers five different loops, each varying in length and difficulty. Hit the Lake to Lake trail for a scenic ride that dips and winds through forests, prairies and swamps. If you’re looking for a higher elevation challenge, ride Blue Mound State Park’s single track 3-mile trail. It’s short, but, perched at the highest point in Southern Wisconsin, it’ll give even the most seasoned riders a run for their money.
Bikeable Miles: Approx 275 miles
Recommended Route: Ride The Quarry, Madison’s ultra-technical trail. It’s a natural roller coaster. You won’t be cruising at uber speed (unless you want to go over the handlebars) but you’ll get a rush from dodging the obstacle-ridden dirt.