The Wolfpack

Distance: 39 miles
Route: TCX / GPX
Ride time: 2-3 hours

Chicago's long industrial history is on display on this ride - as it extends out beyond the reaches of the lake front path and takes you through Chicago's south side (mostly former) industrial corridor. The trip through its working class neighborhoods, shipyards, and finally a splash through the gem of Wolf Lake just over the border in Indiana is a great reminder that Chicago isn't as one-sided as the Northsiders would have you think. On the trip back, you'll be treated to the city's most stunning views of the skyline and lake. If you have a little time, stop in at Plein Air Café in the Hyde Park neighborhood. It's where the Obama's live, and the café is planted right next door to a beautiful Frank Lloyd Wright home.