

There are 62 car dealerships on Western Avenue. There are also ten railroad crossings, two skeevy churches (and plenty of normal-looking ones), one corset shop and at least four catcallers. How do I know this? Because I spent 12 hours walking this 27.3-mile street (the longest in Chicago and possibly the country) from its southernmost spot at suburban 146th Street to Howard Street, where Chicago ends and Evanston begins.
The starting point in Harvey has a highway-overpass feel—Interstates 57 and 294 cross each other nearby, the roads are multilaned and parking lots abound. But as I walk north along the sidewalkless berm on a warm Saturday morning, it quickly begins to feel like country.
Many of the homes look like farmhouses, lacking only a field of corn to complete the picture. One rural-looking abode (13635 S Western Ave), turns out to be the Henry Schuemann House. When Schuemann and wife Ida built the place in 1840, there was only one other home south of the Calumet Sag Channel (13300 S Western Ave).
From 1851 to 1869, Western marked the edge of Chicago, says Peter Alter, a curator at the Chicago History Museum. “People would go to Western to have a picnic in the middle of the 19th century, out in the open fields there,” Alter says.
Up the road, Western crosses into Chicago proper and the neighborhood of Morgan Park, where a man gardening in front of The Healing House (11840 S Western Ave) turns out to be the healer’s husband. The stand-alone alternative medicine clinic has been on Western for ten years. “Before that, it was a pizza parlor,” he says with a laugh. I laugh too, but secretly, my feet are starting to ache.
From there, the road leads through the Irish enclave of Beverly, complete with a rather be broke than a cub fan sign outside of McNally’s Pub (11136 S Western Ave). Things get a little too urban over the next few miles—a lot more asphalt and a lot fewer flowers—and it’s a relief to see a few trees at 95th, where Evergreen Park begins, and wide, fenced-in golf courses appear on the west side of the road.
At Original Rainbow Cone (9233 S Western Ave), a girl who looks all of 14 works the register like an old hand, despite the long line. Between 90th and 81st, the Dan Ryan Woods are a pleasant interlude. Overhanging branches cool me off and a birdsong tempers Western’s divided-highway vibe. At 82nd, Western crosses a set of train tracks, and is suddenly back to “normal”—car noise and auto dealers. It is at this point that my left little toe starts going numb.
Thus begins the most tedious part of Western—what you think of when you hear the words Western Avenue: car dealerships, Subway franchises (the one at 71st cages the sandwich artist behind ceiling-high bullet-proof glass) and dodgy Chinese takeout joints. Some things break the monotony: P. Pa’s Trading Post (4932 S Western Ave) sits in a house’s side yard, and offers leather biker gear and a nice selection of cue sticks. There was also the catcalling (mostly the kissy-kissy noise), which was at its peak during this strip, and kept me on my toes. Kevin’s Hamburger Heaven (4056 S Western Ave) oozes old-time diner character, though the food falls far short of heavenly.
The first quintessential Chicago brick two-flat appears at 33rd, more than 13 miles from the southern origin of Western. The first boutique pops up at 1015 South Western Avenue (Kiwi’s Boutique). While things get generally posher from there, Western never loses its Western-ness, and a car dealership is never more than a few blocks away. Highlights from the northern stretch are the glimpses of Chicago’s past and its gritty present—from the gorgeous old industrial building at 1513 North Western Avenue to the oddly named Western Automatic Music Inc. Building at No. 4206 (it sells jukeboxes). As I pass Rosehill Cemetery, it starts looking like a mighty fine spot for a nap.
Farther north (at this point the bottoms of my feet are burning, bringing tears to my eyes), the city’s multiethnic charms become more evident: Chicago’s only zabiha halal KFC (6732 N Western Ave) offers chicken that’s Muslim-friendly and finger-lickin’ good. Or so the sign says. The Chua Truc Lam Buddhist youth center peacefully shares half an address with the Extra Wide Sock Company (7018–20 N Western Ave). It’s a fine example of how Western can be all things to all Chicagoans.
As for me, that toenail did turn purple, and I had a cough from the car fumes. But I’d walk it again in a second. Just not this second, please.
Plus:
Evanston or bust: I walked all of Western and lived to tell the tale; the same can't be said for one of my toenails.
Photo gallery: See the sights of Western Ave without having to leave your chair.