Group Thru-Hikes 210-mile Chicago Outerbelt Trail for the First Time

If you were a bird soaring above Chicagoland, your eagle eyes might spot a thick, green band: the perimeter where metro fades to country.

This is the “Outerbelt,” hikeable pathways that encircle the city. For years, a connected thru-trail lived only in the imaginations of outdoor enthusiasts who dreamed of being able to walk to Lake Michigan from the western suburbs. But the dream is now reality, thanks to the Outerbelt Alliance, a new nonprofit that raises awareness about Chicago’s green spaces.

On June 11, Jay Readey, Molly Fitzgibbon and Emily Leu became the first people to hike the route when they arrived back at Buckingham Fountain, 210 miles and two weeks after they left it.

The seed of an idea

Readey, a lawyer with a focus on racial justice through investments in distressed neighborhoods, officially incorporated the Alliance last fall after coming up with the idea during a series of walks through the Forest Preserves of Cook County with his mini golden retriever, Copper. Recovering from two partial knee replacements and grieving the loss of his mother, he sought healing in the nearly 70,000 acres of woodland often overlooked by most Chicagoans. “You ask people what’s great about Chicago, and they’ll say the Bears, Blackhawks, Bulls and Museum Campus,” Readey says. “Those 70,000 acres aren’t in that breath, but they should be. We have [preserves the size of] a national park here in our own backyard, and people don’t realize the scale of it, or the beauty and richness of it.”

Readey recalls: “The more I was hiking, the more I was staring at maps and thinking, ‘I could get all the way to Lake Michigan from here. Then, if I could get back across to the Des Plaines River, I could get all the way around the city.’”

The Ohio native was a surprising champion for the circuit—the Outerbelt was about four times longer than the longest trail he’d hiked previously—but he dusted off his decades-old JanSport pack and laced up his boots anyway.

Because the circuit passes through a major metro area, most physical trail infrastructure already exists in the form of parkland and preserves (except for a few stretches of private land the group got permission to walk through). The real trick was stitching them all together and mapping the best route. Each hiker brought a unique perspective: Readey the vision, Leu the experience of hiking 700 miles on the Appalachian Trail (AT), and Fitzgibbon the nature know-how from her job as an environmental educator at the Sand Ridge Nature Center. While Fitzgibbon, Leu and Readey were the main hikers, they were periodically joined for full days and double-digit miles by Alliance board members and members of the public.

Through the Outerbelt Alliance, Readey aims to to get city dwellers outdoors and to diversify the way the outdoors are experienced and marketed in America. “The call of the wild doesn’t do a great job calling to people of color,” he says. “But if we can start close to home, we’ve got a shot. I like to think of the Outerbelt as a gateway drug to the AT or the PCT (Pacific Crest Trail).”

The route

The travelers set out from Buckingham Fountain in Grant Park on May 29. From the fountain, the three headed south, working their way clockwise around the metro area. They followed the shore to the U.S. Coast Guard Station at 98th Street, then cut over and took a winding trail south to Chicago Heights. From there, they made their way through the South Greenbelt Forest Preserve, north between Tinley Park and Palos Heights, and jogged over to the Des Plaines River, which they followed as far north as Rondout before looping back along the lakefront and ending where they began.

“There were all sorts of beautiful, hidden gems that you can miss every day,” says Leu, who works as a market coordinator for REI in Chicago. At the Montrose Beach bird sanctuary, for example, the hikers found themselves among an array of feathered friends in tall grass, insulated from the sound of traffic. “It’s incredible that you can have that kind of experience in Chicago.”

“You can do this over two weeks, or you can take five minutes to disappear into it.”

Readey rattles off his favorite sights they passed on the South Side: Steelworkers Park, Calumet Park, Eggers Woods, Wolf Lake. “There’s a nice string of real jewels that almost know one knows about,” he says. “You can completely get lost to the point where you’re not seeing or hearing anything that reminds you of civilization. You can do this over two weeks, or you can take five minutes to disappear into it.”

During their thru-hike, the group stayed at Camps Shabbona, Sullivan, Bullfrog Lake and Dan Beard for about $20 per night—occasionally having to take a Lyft from trail to campsite. It’s not yet possible to camp as you go because managed campsites don’t exist along the entire trail, but over the next year the Alliance hopes to solicit hiker rates at hotels and develop an Airbnb-style agreement with homeowners who are willing to share their backyards with campers.

Learn More: Interactive Map of Route

A different kind of thru-hike

In American hiking culture, people commonly associate thru-hiking with trekking on famous routes like the Appalachian or Pacific Crest Trails. But the Outerbelt Alliance is helping redefine this notion in one of the United States’ largest metro areas. “Our mentality is that a life outdoors is a life well lived,” Leu says. “If we can get people into outdoor spaces, they’ll start to care about them, and in turn they’ll start to take care of them.”

Preparation is key when attempting a backcountry expedition, from meticulously planning miles and meals to shaving weight from your pack. Hiking through the built world has its perks, however—like LTE cellphone service or the option to peel off the trail in case work calls (as it did in Leu’s case) or your boots need replacing at the Lincoln Park REI store (as they did in Readey’s).

Hiking purists may scoff at a “connected” hike; pulling the plug is often the point, after all. But for the Outerbelt Alliance, the goal is simply to get city-dwellers outside. With the exception of Leu’s AT experience, the hikers who conquered the Outerbelt were relative novices. “We always say, ‘hike your own hike,’” Leu says. “Everyone has their own reasons: Some people are trying to get away, but others want to have a thru-hiking experience that is affordable and accessible. The bottom line is that it’s for your enjoyment.”

Emily, Molly and Jay

Emily Leu, Molly Fitzgibbon and Jay Readey celebrate back where they started at Buckingham Fountain. (Photo Credit: Jay Readey)

The Alliance plans to host the thru-hike each Memorial Day and raise awareness among families who may be surrounded by screens and over-stimulated by city life.

“All we did is prove you can do it,” Leu says. “We met other hikers and cyclists who had been wondering the same thing and were just waiting to see it happen. One of most fascinating things about this experience is that it feels like we grabbed something out of the air that was in everyone’s consciousness, and we just made it real.”