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Hot dogs. Lake Michigan. Da Bears. And excellent trails? Absolutely: The Windy City’s greater stomping grounds offer river-sculpted canyons, quiet hardwood forests, glacially molded ridges, and plentiful waterfalls within easy dayhiking distance. Sample the best of the Midwest on these favorites: Many are lengthy linear trails that let you design your own out-and-back or shuttle trips.
1. Edward L. Ryerson Conservation Area
Trailhead(s): Edward L. Ryerson Conservation Area or Brushwood Center parking lot
Drive from town: 35 minutes
This has to be one of the quietest trails I’ve hiked in the immediate Chicago area. Portions of the trail follow bankside along the Des Plaines River, making for a pleasant sound and view. Ryerson’s 6.5 miles of winding trails and boardwalks through 561 acres allow you to make up your own route. On countless visits, I’ve never replicated the same hike. It’s only a quick 35-minute drive (outside of rush hour) from the Loop, so you can’t beat the rugged feel and accessibility combo.
2. Des Plaines River Trail (Yellow, Unpaved)
Trailhead(s): Allison Woods Trail and Sunset Bridge Meadow Trail access points (various additional access points along trail)
Mileage: 15.4 (point to point)
Drive from town: 40 minutes
This segment (15.4 miles) of the larger Des Plaines River Trail (56.2 miles) is great for folks who live in the near-downtown neighborhoods. You can even get to this trail via public transportation, both by bus and the Blue Line. My favorite section along this trail runs through Dam No. 4 Woods-East, from Thouey Rd. to the S Dee/W Higgins intersection. I suggest parking in the Chippewa Woods lot, walking east on Touhy Rd., and jumping on the trail heading south. This path is also perfect for trail running and mountain biking since it’s very flat and wide with soft soil.
3. Bluff Trail, Matthiessen State Park
Trailhead: Trail begins at Fort
Drive from town: 1 hour 40 min
Matthiessen State Park offers the best of both worlds: beautiful views from atop 45-plus-foot ledges and waterfall drop-offs, and towering sandstone walls from the dells’ rocky floor. I love hiking along the interior trail of the northern dell area during the summer and fall seasons. The dried-up riverbed looks like a rocky staircase and the sides of the canyon make great traversing walls. You also can’t beat cooling off in the summer heat under the chilly water of Cascade Falls.
4. Canyon Tour, Starved Rock State Park
Trailhead: Starved Rock State Park Visitor Center or parking lots at the eastern edge of the park
Mileage: 12.3 (point to point)
Drive from town: 1.5 hours
While popular, Starved Rock State Park is home to some of the best hiking in the state of Illinois. A number of small waterfalls hide between the sandstone walled caverns and winding trails peek in and out of a glacier-carved landscape. When I visit, I park on the eastern edge of the park near Council Overhang (to avoid foot traffic) and head west on the trail towards Hennepin and LaSalle Canyons.
5. Ice Age Trail, Kettle Moraine State Forest, Southern Unit
Trailhead: Pinewoods Campground
Mileage: 31 miles (point to point)
Drive from town: 2 hours
If you’re looking for a proper Chicago-area backpacking (or rugged hiking) trip, the Ice Age Trail is where you’d want to go. Up-and-down valleys offer the perfect amount of elevation and descent. If you have a weekend, I love driving up from the city to camp at the Pinewoods Campground and taking the branches of the Ice Age Trail that pop out of the campground for a dayhike. Thick canopy and evergreen forest surround you on all sides along this trail. The entire trail spans some 1,200 miles, and an elite crew of Midwestern hikers have backpacked the entire length. I highly encourage joining their ranks.
6. Openlands Lakeshore Preserve
Trailhead: Patten Road
Drive from town: 38 minutes
This isn’t your typical backcountry hike, but that’s why I love the Openlands Lakeshore Preserve. It’s a quintessential Chicago experience: a combo of art, community, and nature. The paved paths have quirky, informative interpretive signs and the main trail running down through the preserve’s ravine features a towering, 20-plus-foot-tall underpass mural that’s absolutely stunning. You also can’t beat the serenity of a near-empty Lake Michigan shoreline and quiet prairie land. The preserve is also very ADA-accessible (nice!).