Chicago's OuterBelt Trail Proves Cities Can Provide Access to Nature, Too

The Origins of the OuterBelt

The OuterBelt was officially formed in 2018, emerging from Readey’s personal trail running experiences, fascination with maps, and a vision to create a continuous pathway connecting trails across the metro area. “The idea really began while exploring local forest preserves and realizing it was actually possible to traverse from the south suburbs to Lake Michigan almost entirely on trails, and similarly navigate to the west side of the city without ever touching any highway,” he said.

Thus began an early collaboration with people like Benjamin Cox of Friends of the Forest Preserves and Steve Buchel of Trails for Illinois who helped map the route using a combination of country preserves, Chicago Park District, and Northwest Indiana trails. The first hike, serving as a proof of concept, took place in the summer of 2018 with a small group of four hikers. “When the OuterBelt Alliance officially launched, the early months were magical but logistically complex,” Readey recalls. “The first event required a critical mass of committed people to manage route finding, camping, and coordination with multiple partners, including the Chicago Park District, Cook County Forest Preserve, and REI’s Lincoln Park store who ended up becoming core advisors.”

Trail Details

Today, the OuterBelt spans roughly 210 miles for hikers (about 190 miles are accessible on bike), looping around the west side of Chicago to reach Lake Michigan on the east. It would take you a couple of weeks to hike the entire thing, which is a mixture of relatively flat paved roads, gravel paths and flattened grassy trails especially in some of the forest preserves. Cook County campgrounds like Camp Bullfrog Lake, Camp Shabbona Woods and Camp Sullivan provide overnight options although you can also stay in hotels or Airbnbs.

As I navigated a few different sections, I found that the trail’s flexibility allows both long-haul hikers and day-trippers to enjoy it at their own pace. Readey stressed that understanding access points, rest areas, and trailheads is essential, especially for longer sections connecting multiple preserves and parks. And like any traditional thru hike, it is always wise to check trail conditions, especially along river sections that can be muddy after the rains.

Urban Thru-Hike Highlights

While the OuterBelt spans hundreds of miles, several sections particularly stand out. In the south suburbs, Readey recommended Lansing Woods, Jorgensen Woods, Sweetwood, Glenwood Woods, appropriately called the “Hike the Heights” segment. My favorite was Jorgensen Woods when tall maple trees formed a canopy protecting me from the sun and sounds of large subdivisions nearby.

Within the city, I explored Montrose Beach and the adjacent “Magic Hedge” at the Montrose Point Bird Sanctuary. Stepping into the dense thicket, I immediately felt removed from the city’s noise. “You can hide yourself in the center of it, and the chirping of birds is so loud that you don’t hear anything else,” Readey said. (After visiting it myself, I can report that he wasn’t exaggerating.)

Big Marsh Park, the largest natural area in the Chicago Park District, proved another highlight. Readey called it “a globally significant hemi-marsh,”—a wetland ecosystem with an even mix of open water and emergent vegetation, creating rich habitat diversity for wildlife. As I hiked along the trails, I could see why. Deer grazed in the distance, herons flew overhead, and if you looked closely, you could spot Chicago’s famous skyline in the distance. It was a reminder of how much ecological diversity exists just a short drive from downtown.

Readey also calls the OuterBelt a living classroom of urban ecology. “You can get the solitude in Chicago but then you can also emerge and have these interactions with people who relate to the broader project.”

He recalls conversations with people who shared memories of childhood trips to the city’s forest preserves and how those experiences gave them a lasting appreciation for nature in an urban setting. “Compared to a traditional wilderness thru-hike, where solitude and self are often the focus, urban hikes become culturally rich escapes.”

The trail reflects Chicago’s citywide planning and history as well. Passing through neighborhoods, parks, and riverwalks, I saw firsthand how waterways shape the city’s development and public art in restored parks provide moments to pause and breathe in the city’s identity. As Reedy notes, urban trails are increasingly popular in the U.S., bringing nature into everyday urban life. Cities like Boston (Emerald Necklace trail), Minneapolis (Grand Rounds), and San Francisco (Bay Area Ridge trail) have created connected networks of rivers, forests, and parks, making the outdoors more accessible to its residents.

Challenges and Advocacy

Despite its appeal, the OuterBelt does face some ongoing challenges. The trail passes through a mix of municipal and private land, complicating official endorsement and signage. Certain crossings, such as railroads, pose safety and liability concerns and some remote sections become overgrown if not regularly used, relying on hikers to maintain “social trails” through foot traffic.

Readey emphasizes that the OuterBelt continues as a nonprofit advocacy project. “GPS navigation helps guide hikers through the unmarked sections, and ongoing efforts focus on maintaining the trail, building partnerships, and incrementally improving accessibility and safety,” he says. Fundraising and collaborations, such as those with NeighborScapes, help prepare trails for annual thru-hikes, while detours, side trips, and refinements ensure the route remains engaging and safe.

It's clear there's still work to be done to complete the full vision. The OuterBelt Alliance has published maps for most of the 31 sections of the loop, but there's still one missing. And even when I was using the maps, I found they didn't always match what I saw on the ground, especially when I was traversing and unmarked trail.

The OuterBelt Experience

All in all, even for hikers like me who don't have enough time to complete the entire loop, the OuterBelt provided several memorable sections. Exploring its trails allowed me to experience wildlife like migratory birds, historical sights, and city contrasts in a single outing. “Just the ability to get off the trail at any time and get a Chicago-style hot dog is also unbeatable,” Readey notes, exemplifying the trail’s unique blend of city and nature. And I certainly appreciated this perk. After a day walking around in marshes and forests, nothing felt more Chicago than rewarding myself with a slice of Giordano’s deep-dish pizza.