Dan Ryan Woods

The Major Taylor Trail offers a fascinating journey through Chicago's southwest side, blending urban landscapes with surprising pockets of nature. As you jog along its paved path, you'll transition from the shaded canopy of Dan Ryan Woods to quiet residential blocks, eventually reaching the natural expanse of Whistler Woods Forest Preserve, where deer sightings are possible. A highlight is the cantilevered trailway over the Little Calumet River, providing unique industrial and natural vistas.

Planning your visit is relatively easy, as the trail is well-connected to public transportation and features clear signage, even where it transitions onto city streets. While the route is mostly flat, its 10.9-mile (17.6 km) length and 25 feet (8 metres) of elevation gain make it a substantial outing, typically taking about 1 hour and 48 minutes. This makes it a difficult-rated jog, best for those prepared for a longer effort.

This trail is more than just a path; it's a tribute to Marshall "Major" Taylor, an African American cycling legend, and one of Chicago's earliest urban rail-to-trail projects. It connects two significant forest preserves and features public art, including a 400-foot-long mural honoring Taylor. Its historical significance and diverse scenery make it a standout option for joggers in the region.