1 Des Plaines River Trail
Starts in Des Plaines
The 31-mile Lake County portion of this route extends nearly to the Wisconsin border. A gravel path meanders through oak forests, prairies, and wetlands. Wildlife abounds — deer, chipmunks, turtles, butterflies, and snakes. Hungry? Hit the Shanty in Wadsworth, a 50-year-old institution whose whiskey shrimp and tequila salmon are so beloved that Guy Fieri featured them on the Food Network twice.
2 Sheridan Road
Starts in Evanston
Keep heading north at the end of Chicago’s Lakefront Trail, and you’ll pedal right into one of the region’s most popular routes for group rides. Competitive clubs like Team Judson may fly by, but now that there’s a dedicated bike lane in Evanston, even leisurely riders will feel safe on the streets. For longer outings, cut west on Lincoln Street and then north on Poplar Avenue to pick up the Green Bay Trail in Wilmette.
3 Skokie Valley Bike Path
Starts in Highland Park
The 9.7-mile Lake County section of this trail — nestled between a roadway and train tracks, with power lines overhead — doesn’t always offer the best views (and, despite the name, travels through Highland Park, Lake Bluff, and Lake Forest, not Skokie). But what it lacks in ambiance, it makes up for with wide, uncongested opportunities for superfast riding over smooth asphalt.
4 Tinley Creek Trail
Starts in Oak Forest
Take your pick from this network of loops and spurs. Start at Yankee Woods (on Central Avenue), where you’ll find a map and access to several routes, all paved. Rides range from one-mile out-and-backs to the 9.4-mile Red Trail, which runs through Rubio Woods and around Arrowhead Lake. Glaciers left behind gentle inclines; wildflowers line the paths in the spring, and colors abound in the fall.