How My Local, No-Frills Walking Trail Helped Me Heal from a Breakup and Find Love Again

published May 28, 2022
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Credit: motorolka/

A few years ago, I was going through a breakup. And when I say “going through,” I mean I was harnessing every available shred of might to push through it. Processing each bit of knowledge, engaging any whisper of advice, and applying every lesson I’d ever learned from previous breakups, I prepared for this journey to the other side — no matter what that vista might have in store. And oddly, together two things gave me the momentum to see myself through: my local trail, and the Cheryl Strayed memoir “Wild.” (And sure, the film adaptation starring my personal icon, the incomparable Reese Witherspoon.)

In her best-selling memoir, Strayed recounts navigating through grief, trauma, and the end of her marriage. Armed with plenty of supplies but minimal experience, she set out to hike the Pacific Crest Trail solo. Reeling from my own heartache, I clung to the soft, feathery pages of my used copy. I was determined to activate my own “Wild”-like transformation. Only, I had no intention of hiking cross-country, or even outside the Cook County border

One of Chicago’s most beloved outdoor spaces is its Lakefront Trail. Along Lake Michigan, the Lakefront Trail features paved cycling and running paths from the north side’s Ardmore Avenue all the way to the south side’s 71st Street. The view of Lake Michigan stuns year round, whether sailboats dot the summer waters or ice encrusts the rocky banks. This is not your average trail. And despite its fame and inspiring imagery, it wasn’t my trail.

Through frigid mornings and overcast afternoons, I peeled myself out of bed/off the couch/away from my phone (a hell box of bad memories and impulsive temptations for a newly-single and devastated person) and embarked on the humble trail. Starting at my apartment, I’d traverse the handful of blocks to the Lincoln Park neighborhood’s namesake park: the Windy City’s largest public park, spanning seven miles along the north side’s lakeshore. 

Credit: fukez84/

Where Diversey meets Cannon, a simple dirt-and-gravel path beckons city dwellers out to nature. Sure, the Midwest doesn’t offer the desert hikes of Arizona, nor the tricky terrain of Colorado. And Chicago definitely cannot guarantee pleasant weather. But my low-commitment daily jaunts took me out of the stench of my own pathetic, wallowing thoughts provided me perspective and comfort that nary a social media-stalking session could supply. 

The simple act of taking a carefree walk along a no-frills trail was healing. No matter what anyone tells you, you don’t need to make any purchases to achieve wellness — no hiking boots or backpacks or tents required. Clad in my Tevas or tried-and-true Doc Martens or beat up sneakers, I worked these treks into my post-breakup routine and eventually felt my emotional burden getting lighter and lighter.

As it turns out, if trekking PCT is out of the question, you can get lost and find yourself all over again just as easily on your local, average path. Along the path, I was just another person, undefined by my heartache, loss, or the blank slate of what was to come. I didn’t have a mountain to climb or a river to ford, but I had plenty of obstacles to overcome that weren’t as obvious as the nearby playgrounds or ponds. 

Just as Strayed’s memoir ended with a glimmer of hope for her healing, so does my trail. It’s been a few years since my winter of wandering, and I wish I could go back in time to cross paths with myself out in Lincoln Park. I’d tell myself it will be okay, and that this too would pass, and that this coming October, I’ll be getting married in that same park, along that same path, to an excellent dude who has made every lesson worth it. Wild, indeed.