Major Taylor Bike Trail
Beverly to Riverdale
Distance: 8 miles
Head south from the Dan Ryan Woods at 81st Street to the Whistler Woods Forest Preserve at West 134th Street, following an unused train line. You’ll traverse forests, parks, and historic neighborhoods like West Pullman and Beverly. Along the way, you’ll find Original Rainbow Cone and Top-Notch Beefburgers, perfect spots for a pit stop.
East Side to Hegewisch and back
Distance: 5 miles
Ambitious cyclists can bike the additional 2.7 miles to the trailhead from Calumet Park (the lakefront park, not the village), giving them the chance to bike under the Chicago Skyway. Others can start a leisurely loop from the Eggers Grove Forest Preserve. That’s a former antiaircraft missile site, so keep your eyes peeled for a Cold War–era warhead on display near the picnic tables. You’ll bike through a number of habitats — savannas, wetlands, woods — and ride past Wolf Lake, popular with fishermen and boaters. Hike around William Powers State Recreation Area before looping back.
North Shore Channel Trail
Evanston to Lincoln Square
Distance: 7 miles
Begin this family-friendly trail (underpasses let you avoid car traffic) at the Ladd Arboretum, following the North Shore Channel south. You’ll wind through hills and trees before coming to the colorful, oversize art at the Skokie Northshore Sculpture Park. Cross the pedestrian bridge in Lincolnwood and head to Legion Park, where you can stop and catch the mist off the fountain. At River Park you’re back under tree canopy and are bound to catch a few soccer games. Finally, stop for a banh mi at Nhu Lan Bakery.
Northerly Island Park
Distance: 1 mile
A far cry from its former life as Meigs Field, this nature preserve is now filled with prairie flowers, grasses, and gorgeous views of the lake. The path itself is short but sweet, so it’s great for kids. For a longer, less isolated ride, head just south of the Shedd Aquarium, where you can connect to the Lakefront Trail. The Northerly Island path is closed on occasion for repairs due to erosion, so check with the Chicago Park District first.