The Bloomingdale Trail

Bloomingdale TrailClick here to see more photos of The Bloomingdale Trail
Photo Credit: Gene Wagendorf III

In a city with so many people, there isn’t much in the way of hidden anything. Sure, people like to refer to their favorite out of the way bars and restaurants as “hidden gems” and a park district bike path that weaves through a forest preserve might have the charm of seclusion. Some of the city’s smaller beaches have a tucked away feel that makes a visit feel particularly enchanting, making the place feel almost your own. I love places like this, and have tried to write about them — Stearn’s Quarry and Promontory Point, to name a few. But these places aren’t truly hidden. The Point is packed with visitors all summer long and the Quarry is quickly becoming a well-known leisure spot. In a city with a rich and well documented history, little is forgotten. Little is left truly abandoned. The Bloomingdale Trail may be one of the best examples of a lost territory, a place that seems to exist outside the context of the rest of Chicago’s urban shuffle.

That isn’t to say it’s a secret. People know about it, but their numbers are few. Even fewer is the number of people who’ve been. The information is cloudy — who exactly owns the property? Is it a park? Will it become one? Where the hell can I get up there? What makes the Trail so special is that regardless of the bureaucratic arguments, the financial tug of war between the city and the Canadian Pacific Railway, the proliferation of online photo blogs with Trail pictures and the clear evidence of other visitors (graffiti, broken bottles, candy wrappers, etc.), this place still feels hidden, feels secret. You can’t just walk through a tunnel or a gate, you have to sneak your way on. You won’t see a water fountain or a bathroom or any of the city’s infamous black fences. The grass is mottled with old gravel, the tracks and ties are rusting. In the middle of some of Chicago’s most well-traversed neighborhoods it becomes possible to be outside and be alone. To be unseeable. To disappear into the middle of the day like a ghost.

After visiting the Friends of the Bloomingdale Trail’s website and after reading an article in The Reader about the various security issues involved in having a relatively unsecured, unpatrolled stretch of elevated track behind homes and parks, I had to visit.

So I stood on the corner of Leavitt and Milwaukee, peering up at the tracks on a Sunday afternoon. They looked like any other tracks. I lit a cigarette and squinted up past the sun. How in the hell was I supposed to get up here again? The easiest entrance I found on the eastern end of the trail isn’t exactly the most secluded, but if you’re quick enough and casual enough, especially on a lazy Sunday, the passing cars and pedestrians seem indifferent to a few people slipping between a fence at Milwaukee and Bloomingdale and struggling up the side of a hill. A gentleman washing his car in the alley took notice, shook his head, having presumably seen this many times before. We came up on the bridge over Milwaukee and immediately I felt this was going to be worth it. The tracks, overgrown with grass and weeds, seemed to stretch on forever, and better yet, there wasn’t another person in sight.

We started by heading east. The trail dead-ends near Ashland into an embankment blocked by a chain link fence, but a small, door-sized hole had been cut and peeled back. The warehouse-style walls were covered in neon paint: a purple Pac-Man eating yellow dots and several memorials to the late King of Pop. A chair, a few filthy mattresses and some moldy books littered the far corner of the space. Someone, or someones, lived here. The whole space felt haunted by its still-living inhabitants. They’re a kind of ghost, societal ghosts at least, despite the still working lungs and hearts. A different kind of spirit than the large Pac-Man ghost spray painted near the entrance. This was the only place on the trail where I actually felt like I was intruding, trespassing, and so after a few quick snap-shots we turned to head west.

The tracks move past the south end of the Churchill Field Dog Park, which provides a nice few minutes of entertainment watching dogs wrestle over tennis balls. A kickball game in the adjacent field regularly yielded popups towards the track that always looked like they’d make it to us. None did, but we were prepared to throw them back, in true Chicago style.

Past a rusty saw, a few more smashed bottles and CDs, we came across a stretch of rail covered in anonymous confessions, like the ones you might find on Group Hug. Sweet laments like “I still miss my mother” rested in silver ink next to more laugh-inducing proclamations like “I wanna write a book about jackin’ off.”

At Western the distance between the Trail and the roof of a gas station and car wash was too inviting. After I made the short hop over I was treated to an excellent bird’s-eye-view of the big soaked furry spinners that swirl over filthy cars. There were several plastic viewing areas, almost as if the station owners were asking for people to come take a gander.

The condos and apartment buildings running parallel to this stretch of track seemed conflicted about how to embrace the locale. A few gardens, nice shrubs and flowers, had been planted and fenced off on the trail, clearly the work of people who were pro turning the Bloomingdale Trail into a park. Others had erected high privacy fences that hid snarling dogs all too happy to bark and growl at the hint of a passerby.

Approaching California there was a giant uncovered manhole that just begged for a Ninja Turtle to pop out. No such luck, and I resisted, smartly and regrettably, to venture down looking for one. A small wooden board had been kicked off to the side simply read “Love is lost.”

One of the sweetest views was from the bridge was over Humboldt. The tree-lined boulevard stretches north from Humboldt Park looked more serene, more friendly, from up above. At this point the sun was blazing and the leaves on the trees looking so green they were almost transparent. Another small garden of prairie grass and flowers was running wild near the side of the tracks, a simple collection of plants that had apparently decided if no one else was going to use the trail they may as well go wherever they pleased. There was more graffiti, a little more sinister farther west that included things like “Kill All Police” and various gang signs and announcements of sexual conquests.

Farther west, past Kimball, we came across a series of abandoned rail cars. Rows of what looked like old coal cars and a few tankers made up a sort of degenerate play ground. The wheels and cranks still moved, chains still lurched around gears. Ladders and platforms, rust free, were not to be resisted. Whereas the rest of the trail offers interesting things to take pictures of — views, paintings, funny slogans in paint — this was the spot where I wanted to be the center of the picture, hanging off of one thing, climbing on another. There was more interesting art there too. Whole sides of tankers had become amateur murals and canvasses for amateur advice. One slab of steel encouraged me to “Die Fast”. Another had a frowning pig encouraging me to eat my vegetables.

Bloomingdale Trail ends just west of Lawndale at an old boxcar where the tracks split off and trains still come whizzing by. The boxcar was locked and there were a few parked cars at a still operational control tower. I grabbed a souvenir rail spike from a large pile and began the trip back. Back to Milwaukee avenue. Back to Chicago.

Gene Wagendorf III

About Gene Wagendorf III

Gene is a writer who has spent his entire quarter century of life as a resident of Chicago. When not exploring the city he can be found wandering flea markets and garage sales or having a cigarette between classes at Northeastern Illinois University, where he hopes to acquire a degree in the next quarter century. His favorite smells are old books and bowling alleys. His poetry (how embarrassing!) can be found in issues of Kill Poet, Ditch, Word Riot, O Sweet Flowery Roses and Vowel Movements.

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