The Northwest Passage: Walking the Length of Elston Avenue

Rob Reid, Mike Filipski, and Elisa Addlesperger. Photo: John Greenfield

[This article also ran in Checkerboard City, John Greenfield’s column in Newcity magazine, which hits the streets on Wednesday evenings.]

I’ve walked the entirety of 11 Chicago streets in order to experience aspects of the pedestrian environment, plus local architecture and culture, that I might have overlooked using faster modes. So when Rob Reid, who writes the history blog Avondale Time Machine, invited me to join him and his friends to hike all 9.5 miles of Elston Avenue last month, I couldn’t say no.

The street’s namesake was Daniel Elston, a London merchant who immigrated to Chicago in the early 1800s. By 1830 he’d bought a 160-acre parcel in River West, located along a meandering wagon road then called the Woodstock Trail. The multitalented settler established several businesses, making soap, candles, bricks, beer and whiskey; he also served as a school inspector and an alderman, and founded a bank. While Elston was first living by the trail that would later bear his name, it was a plank toll road owned by Amos Snell, who charged travelers 2½ cents per mile to travel it. Displeased with this, local farmers staged a Boston Tea Party of sorts – they dressed up like Indians, chopped down the toll gates and burned them.

Nowadays, Elston parallels the Kennedy Expressway, and it’s a popular alternative for drivers trying to avoid expressway traffic jams, but it’s also a useful bicycle route, providing a relatively mellow alternative to hectic Milwaukee Avenue. Last year the Chicago Department of Transportation installed one of the city’s nicest protected bike lanes on the street from Milwaukee to North. Elston and Milwaukee are the only two streets in the city that intersect twice; pedaling north on one and then returning via the other is a circuit called “biking the knife,” for a reason that’s obvious if you look at a map.

The Elston Avenue protected bike lane at Division Street. Photo: John Greenfield

I show up at the south intersection of the two streets, just north of Chicago, a few minutes after the 5:30 p.m. meeting time and don’t notice Rob and his crew, so I hang out for a few minutes observing the massive amount of rush hour bike traffic on Milwaukee. Assuming the others have taken off already, or else that I’ve gotten the date wrong, I start walking north on Elston solo, hoping I’ll catch up with them at a tavern up the street.

The protected lane features smooth pavement, green paint at conflict points, and lines of flexible posts and parked cars to keep motorists out, but I see only a handful of bikes here, since it’s not as direct a route northwest as Milwaukee and has far less retail. Elston is generally an unwelcoming environment for pedestrians, with narrow sidewalks, some dangerous street crossings, and views mostly of industrial buildings, garages, gas stations and big box stores, but there are some gems along the way. Climbing a small hill to Division, I turn around and enjoy a stunning skyline vista.

Just before Division, Elston began curving northwest. I pass by the Morton Salt umbrella girl logo painted on the roof of the company’s massive riverside factory, and then arrive at North Avenue, where men with cardboard placards are asking motorists for change. Above them, the spinning sign for Stanley’s Produce features a caricature of the founder smoking a pipe, riding an airplane shaped like a watermelon. North of North, the protected lanes disappear and the street has a more desolate feel.

At Ashland and Elston. The pink mustache identifies the car as a Lyft on-demand ride-share vehicle. Photo: John Greenfield

At Cortland I pass by the Star Carwash, then come to the Horween Leather Factory, 2015 North Elston. One of the oldest tanneries in the country and the only one left in Chicago, it’s the exclusive supplier of leather for NBA basketballs and NFL footballs. It sits at the six-way junction of Elston, Armitage, and Ashland, one of the city’s worst intersections to navigate on foot or by bike. The dauntingly long crosswalk on the north leg of the juncture is almost completely faded, and I keep a keen eye for turning cars as I hustle across it.

A few blocks later I’m at Elston/Fullerton/Damen, much-hated by drivers, although I’ve never had any problem getting through it on a bike. To reduce congestion for motorists, next year the city will spend more than $36 million to reroute Elston through what’s now the front lot of the Vienna Beef hotdog factory so that it bypasses the junction. Unfortunately, WhirlyBall, where you can play an odd hybrid of polo, jai alai and bumper cars, will be demolished as part of the project. Vienna Beef plans to relocate to Bridgeport, and WhirlyBall will be moving to Lincoln Park.

Outside the Vienna Beef plant. In the future this space will be occupied by the Elston bypass of Fullerton/Damen. Photo: John Greenfield

After passing through the big box store hell zone between Fullerton and Logan, I catch up with Rob and his friends at Frank and Mary’s Tavern, 2905 North Elston, an old-timey Avondale pub. Along for the walk are Elisa Addlesperger, who contributes to his blog, and Mike Filipski, another avid historian.

When I tell them I started my walk at the intersection of Elston and Milwaukee, there’s a moment of confusion about whether we started at different Elston/Milwaukee junctures and are only crossing paths now, like the north- and south-going Zax from the Dr. Seuss story. Fortunate we figure out that we’re both going the same direction. Beneath stuffed deer heads, mounted bass and the famous “Avoid street congestion” ad for the ‘L’, we raise a toast to Daniel Elston.

Alywind Musical Instruments, 3219 North Elston. Photo: John Greenfield

We exit the tavern and stroll back into the hot spring evening, with the setting sun turning the sky a soft pink. At 3219 North Elston we come to Alywind Musical Instruments, a careworn storefront labeled “Accordians” (sic) in crooked pink vinyl letters. Owner Bea Zimmerman plays the squeezebox in Rob’s folk band the Astrohillbillies.

By the time we reach the Kelly Eisenberg hotdog factory, near Addison, it’s dark and a half moon hangs in the sky. After passing through a lovely cloud of honeysuckle scent around Drave Avenue, at Irving Park Road we have to make an inconvenient right-angle crossing, traversing the street twice, in order to continue northwest on Elston.

Phixx606Cycles. Photo: John Greenfield

Phixx606Cycles, 4075 North Elston, is a new bike shop specializing in custom fixed-gear bikes, for a young, Latino clientele, reflecting the growing popularity of the affordable speedy bikes with city youth. It’s a sultry night, and up the street teenage girls are hanging out on the sidewalk in plastic chairs.

The Two-Way Grill, a slender greasy-spoon wedged between Pulaski and Elston near Montrose, is reminiscent of Edward Hopper’s “Nighthawks at a Diner.” This area is the center of Chicago’s North African community, anchored by the Muslim Community Center, 4380 North Elston. There are a number of Moroccan, Algerian, and Tunisian businesses here, including boutiques, restaurants, delis and bakeries.

The Two-Way Grill, Elston and Pulaski. Photo: John Greenfield

It’s really warm out now, and I’ve started to break a sweat as we stride, which is unusual for me. After crossing over the Edens Expressway, on the 5100 block of North Elston we come upon the Trinity Slovak Lutheran Church with a slender concrete spire in front, topped with a crucifix. Across the street are the Knanaya Catholic Society and the Bong-Bool-Sa Temple, a storefront Korean Buddhist sanctuary.

At Foster, Rob takes us just west to Rabbits Bar & Grill, 4945 West Foster, one his favorite dives, which happens to have an excellent craft beer selection. As we’re bellied up to the bar, a thunderstorm materializes out of nowhere, with rain blowing at a 45-degree angle. Elisa, a bit delirious from all the walking, phones her husband for a ride home.

Rob and Mike at the northern intersection of Elston and Milwaukee. Photo: John Greenfield

At last the guys and I reluctantly venture into the downpour. We trudge past a DMV facility, the CTA’s Forest Glenn bus garage, and a seemingly endless series of squat, beige postwar two-flats. I regret that it’s too late to stop in at Smak-Tak, 5961 North Elston, a chalet-like Polish eatery known for having some of the best pierogies in town – its name translates to “Taste-Yes!”

Finally, drenched, we reach the northern juncture of Elston and Milwaukee, at about 6200 North, in the Norwood Park neighborhood. As the guys duck into nearby Jet’s Public house for a final pint, I take shelter under an awning and call the Regional Transportation Authority’s travel info hotline looking for a transit option.

It’s about midnight, the #56 Milwaukee bus has stopped running, and the guy on the other line apologetically tells me there’s virtually no way to get home to Logan Square by transit at this time of night. The flickering neon sign of the adjacent Esquire Motel flophouse beckons me to rent a room. Fortunately, it turns out there’s a taxi office near the bar, so I’m soon warm and dry in my own bed.

  • Michael Weiser

    Nice report, John. My wife and I had a pre-wedding party at Whirly Ball. Sorry to read it’s being forced out, but happy that it’s relocating.

    I’ve tried using Elston as a Kennedy alternative, but it’s not much good when coming from the airport to Ohio.

  • John Amdor

    Excellent story. My girlfriend and I took a walk through Graceland Cemetery on Sunday and came across Daniel Elston’s grave. I wasn’t sure if it was street’s namesake or not. Glad to know it was.

  • Joseph Booker

    Small correction: “Elston and Milwaukee are the only two streets in the city that intersect twice” – and are other pairs (unless you count N Sheridan and W Sheridan as separate streets)

  • Mcass777

    I ride the entire length of Elston everyday. Great street and when it’s not too busy, surprisingly bike friendly. I think the numerous machine, auto and repair shops create less traffic than dry cleaners, starbucks, and bars – those make Lincoln tough to ride. Thanks for the great info on some of the quirky storefronts. You did forget Paul Sherman Photography just south of Irving Park. The place was the site of a large pot growing bust a few months ago!

    Great post!

  • BlueFairlane

    Other than the hell stretch between Fullerton and Western, I’ve always found Elston a very pleasant ride. I’ll take it over Milwaukee any day.

  • Fbfree

    Well, it’s disqualified because it intersects 3 times.

  • Louis Silverman

    I was going to mention the same thing, you must be ignoring Sheridan/Broadway because they intersect thrice.

  • Elizabeth

    Interesting idea! Do you have reports published about the other streets you’ve walked?

  • Thanks!

  • I stand corrected. Thanks!

  • Thanks John.

  • John

    Nice one, John. I love your street walking articles. Any plans to collect them into a book of some sort?

  • Anonymous

    Used to hang with my Dad at Sipi Metals on Elston. Walking the street articles are great.

    No way to get home by transit – classic.

  • Thanks! Twist my arm?

  • Jake

    I love the industrial buildings. Some may considerate it not good to look at, but I think it has it’s own charm. A city at work. That’s what I love about Chicago’s streets like Elston.

  • Anonymous

    Try the Blue Line.

  • Jeff Weiner

    The City’s proposed “solution” for Damen-Elston-Fullerton will be anything but. All the previous improvements just added to the congestion, and I speak with some authority as a retired traffic engineer with 27+ years as a City employee/

  • Anonymous

    That google map matches one of joseph’s. The third is at 3900 n broadway.

  • Anonymous

    Pretty sure it’s just moving up to Elston & Webster last I read (somewhere by ReBuilding Exchange)

  • Cis

    I’m walking the Prairie Path, in sections! Then I’ll do the Great Western trail. It’s been a wonderful experience. I’ve walked all of Edgebrook. Elston was a great idea.

  • Kelly Pierce

    I walked Elston from Addison Montrose last year. What struck me was
    the pollution and dirty air. I could feel diminished lung capacity from
    it all. Walking just two or three blocks from Elston allowed me to
    feel better air again. John, did you notice the increased pollution and
    dirty air on Elston compared to other streets? A few months after I
    walked Elston, I heard that the state representative in the area, Deb Mel, was
    diagnosed with breast cancer. I understand she lives in the triangle
    between Elston and the Kennedy expressway and grew up around Elston.
    I wonder if all this pollution impacted her health.

  • Awesome! If you write about your experiences, please send us a link that we can share with our readers.

    Here’s my writeup of walking 40 miles for my 40th birthday from Logan Square to Aurora, including sections of the Prairie Path:

  • Agreed, although, hopefully the Elston bypass will include the city’s first raised bike lane:

  • Although Elston is generally gritty and unpleasant, I didn’t notice particularly poor air quality, but I’m not that sensitive to such things.

    Man, I would never want to live next to an expressway. It can’t be good for your health. My friend Dave “Mr. Bike” Glowacz sold his nice house near the Kennedy a few years ago for this reason. That decision probably added years to his life.

  • Gregory Jay Valent

    Interestingly, Chicago magazine had a thread back in the 1970s about the same multi-intersection streets. An article was written about Milwaukee – Elston, and the following month, letters were posted about Sheridan – Broadway. Some things never change. BTW, you walk two blocks from my house and don’t stop by ? (And you didn’t mention Tony’s Finer Foods !)


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