I set out to walk 210 miles around Chicago Here's how it went.
Midwest Living|Spring 2024
I STEP INTO THE WOODS, take a big breath in, let out a heavy sigh, and feel tensions drain.
DIANE PENNINGROTH
I set out to walk 210 miles around Chicago Here's how it went.

The soft dirt path below stretches for miles; around me are a dizzying number of sun-dappled shades of green, with bright blue sky and dark-as-night trees poking through. Around a bend, yellow wildflowers pop out of the underbrush, where curious deer and rustling ground squirrels (squinnies to this Iowan) startle. Overhead, a shadow passes. I grab my camera to catch it-not a hawk or an owl, but a plane coming in to land at the airport less than 5 miles away. The juxtaposition of scenes feels surreal until I remember: I'm in Chicago.

Mid-pandemic and filled with wanderlust, my husband, Tom, and I bought a condo in the city for long getaways and more time with our two adult kids who live there. Keeping our home base in Des Moines, we toggle between two very different living styles in neighboring states. We're equally happy hiking and exploring rural Iowa as we are hustling through busy streets to catch the L train for a night of live music. So when I heard about the Chicago Outerbelt, a 210mile trail that encircles the entirety of the city, I was intrigued. I set a summer goal: Complete as many miles as I could and learn more about our new part-time home.

The trail is the brainchild of outdoors enthusiast Jay Readey, who cofounded the Outerbelt Alliance with Benjamin Cox, Emily Leu and Molly Fitzgibbon. The nonprofit's mission is to promote eco-recreation in metro environments and engage diverse communities in outdoor experiences. Chicago has an astounding network of rec trails and green space, many found along rivers and lakes. (There are 70,000 acres of preserves in Cook County alone!) The Alliance mapped one big, grand loop by charting connector routes between existing trails. "The waterways did the work for us," Readey says. "We just needed to connect them."

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