Ride a paved stretch through diverse landscapes
Start at Centennial Trail in Lemont, end at Cicero Ave in Alsip
Distance: 13.3 miles (one way)
Even experienced riders welcome the relatively new, multi-purpose stretch of the Cal-Sag Trail in the city's south suburbs in Palos Park. Eventually, the pathway will expand to 26 miles and connect to other trail systems like the Centennial and I&M Canal trails to the west to the Burnham Greenway to the east. Riders can take in the landscape diversity along the Cal-Sag Channel, including some hills. Park near Archer Ave and Calumet Sag Rd in Lemont or access the trail via Sag Quarries, Teason’s Woods, among other spots.
Hit one of Chicago's best museums and Indiana's best brewery by bike
Start at The Museum of Science and Industry, end at 3 Floyds Brewpub in Munster, IN
Distance: 21.6 miles (one way)
Beer geeks can meet up at the Museum of Science and Industry before departing on a 40-mile lakefront ride from Downtown to one of Indiana's best brewpubs. The Lakefront Trail gives way to streets on the city's South Side before connecting to the Burnham Greenway, Wolf Lake Trail, and Lake County Monon Trail, which will carry you over to 3 Floyds for top-notch beers on tap and a few rarer bombers to stockpile. Push through the urge to nap by first biking another 10 miles west to Flossmoor Station Brewing Company -- conveniently located at the Metra stop -- for another growler to share on the train back to the city (remember to politely ask for disposable cups). You can at least tell your friends you biked all the way to Indiana just for some beer, even if you couldn't pedal your way home.