The Lakefront, Chicago, IL

You'll need all the wind at your back that the Windy City can provide to complete this ride. The Lakefront Path stretches 18.5 miles alongside Lake Shore Drive and Lake Michigan and runs to Chicago's South Side. One of the path's hotspots is Navy Pier, where you can skate the one-mile promenade or enjoy live entertainment. For skaters who really want to got some air, the Navy Piers Ferris wheel offers spectacular views of Chicago's skyline. And if you get overheated on your skate, no sweat--just kick off your skates and go jump in the lake!

National Skate Patrol volunteers offer free braking clinics and skate maps.

For more information on Chicago's skate scene, check out Get Inline Chicagoland.