One definition of a roadway is: “The land over which a road is built; a road together with the land at its edge.” From a utilitarian perspective, roadways offer mobility for people and vehicles, allow for business and commerce, and certainly provide boundaries between communities.

But roadways also can be pivotal in defining a city—and perhaps even defining a person—through what a roadway could influence and instill, especially over decades and across monumental changes to the very fabric of an urban environment. Perhaps it could do the same to a person.

He wholeheartedly supported that perspective about Milwaukee Avenue, one of the diagonal arterial roadways emerging spoke-like in a northwest direction from Chicago’s central core, a bastard thoroughfare that challenged the city’s logical north-south/east-west grid system, an anomaly that created its own kind of order.  Milwaukee Avenue, which spans some 10.5 miles within the city, probably was among the many trails used by the Native American tribes – the Ojibwa, Ottawa and Pottawatomie—who inhabited the land now Chicago. It provided these peoples with a gateway to and from the river and swampy lakefront to the forests and glens a few miles away.  Later, when the aboriginal peoples were pushed north beyond the so-called Indian Boundary line, white settlers monetized what became known as Old Plank Road by adding a “toll booth” of sorts in what’s now the Logan Square neighborhood.  The farmers used the road to transport produce into a Chicago emerging into a true city following the great conflagration that changed its course forever.

For him, this history proved fascinating, as was the fact the trajectory of the road, swaying away from downtown and the lakeshore, resulted in a handful of six-corner intersections every couple of miles. No roundabouts were built where these divergent streets met, however all eventually matured into communities of their own, all bound by that one angled road.

For some years, he felt it imperative to chart segments of his own history during a life lived, for all but a handful of years, within a relatively short stroll of Milwaukee Avenue. What follows are thoughts and observations, often rambling and accurate to the best of his recollection, of his favorite street in the world. 

A Thumbnail Perspective

Originating at Lake Street on the fringe of what decades ago was downtown, the Milwaukee Avenue he first knew provided the address for small manufacturing businesses and modest industrial concerns, ethnic grocery stores and no-frills restaurants, Polish bakeries managed by immigrants, owner-occupied brick apartment buildings with impressive and often ornate brick facades, once grand movie theaters, single-room-occupancy hotels that were seedy even back then, long gone department stores that anchored a retail district, no-frills bars and liquor establishments frequented by  working men and neighborhood rascals – and for a while, the tallest office building outside of the Loop. The street provided an address—and perhaps an identify—for business, commerce, culture and existence for generations of Chicago residents.

In the roadway’s shadows were the churches, architecturally stunning structures that still serve as testaments to the conviction toward permanence European immigrants (including his Polish ancestors) brought to United States well more than a century ago. None of these mostly baroque-styled houses of worship actually front Milwaukee Avenue, but many worshipers traversed the street to get to and from mass, school and services on the holidays. The parishes were the spiritual, cultural and social centers for three generations before their congregations dwindled dramatically throughout the 1970s.

The #56 CTA Milwaukee Avenue bus also helped define the street. Back then, those usually loud, un-air-conditioned green transit behemoths spewed diesel smoke and shepherded people to jobs and schools, stores and parks, before terminating downtown at Michigan Avenue and Washington Street, or way, way north in Niles, where the city ended and the Cook County Forest Preserves began. The bus provided mobility for those without automobiles in the decades before rapid transit was extended beyond the old elevated station at Logan Square. How many times, he wondered, had he boarded the 56 bus as a kid, paying 12 cents to travel the two-plus miles downtown to exit at State Street when it truly was a great street, with a half-dozen movie theaters and sprawling department stores, magical places open to everyone. 

And, of course, there were the people. There were sons and daughters of immigrants, the men still wearing hats, the women still wearing floral patterned dresses. There were the merchants, Jewish men with wide smiles, pronounced accents and an uncanny ability to fit you into the right Holy Communion jacket your mother would like (and purchase).  There were the DPs, or displaced people, the refugees from the old country who finally found a better life through a factory job and second-floor apartment. There were the bums, often slovenly in appearance but generally passive as they staggered or sat passively in an alley or doorway, a half pint empty beside them. And, there were kids like himself, walking in groups, swaggering and swearing, heading to nowhere in particular but some place that got them away from home for a few hours to experience Milwaukee Avenue as it was in the 1960s and parts of the decade that followed.

Although it took him decades to realize it, the Milwaukee Avenue of his youth served as a linear microcosm of the world he came to know. And, that world, now best known by its official name of West Town or to be more precise, Noble Square (but always “the old neighborhood” to him) revolved around all things Chicago. The street provided an escape in the direction of the “better neighborhoods” to the north and to everyday encounters with the always-evolving polyglot world of Poles, Jews, Hispanics, African Americans and new arrivals from the south he and his friends called “hillbillies.”

Milwaukee Avenue was a conduit that helped shape him as Chicago, a city of neighborhoods, continued to evolve.

The Initial Memories

Literally a minute’s walk from his childhood home on Walton Street, Milwaukee Avenue (“Milwaukee Avenoo” in the now-gone Chicago vernacular) was the gateway to his grammar and high school and the homes of the uncles, aunts and cousins who lived near St. John Cantius parish. From kindergarten through 6th grade, each weekday during the school year he, his brother and sometimes his grandmother, better known as Busia, would trek south across the section of Milwaukee Avenue that spanned the Kennedy Expressway and a few blocks further to attend church and then class at St. John’s. Yes, even in inclement weather—snow, rain and sleet—he walked.

He has faint memories of what his neighborhood was like before engineers drew up plans to build the expressway and carve a broad swath of concrete through parts of the city north to south, east to west; but one his earliest and most lasting memories was seeing the Milwaukee Avenue bridge span in the distance just seven or so houses to the east, with the traffic below sounding at times like an unceasing march of mechanical bees. The arch supports were always a dull green, the metal guard rails always were a dull grey and the superstructure a dull aggregate; they still look this way today.

Below the block-long span, cars and trucks inched their way to and from the direction of downtown, much as traffic conditions exist today.  When traversing the bridge, he could see what remained from a neighborhood carved by that eight-lane modern limited access highway:  A small metal fabrication shop, brick and frame two-flats like the one he grew up in, Eckhart Park with its baseball diamonds, old-school playground and Prairie style park house, and of course, the massive mural adorning the back wall of the Polish Roman Catholic Union, an imposing brick edifice that housed offices for a fraternal organization and insurance concern, as well as a museum he visited only a handful of times in his life.  And, for a time, he and his brother would ride skateboards down the bridge, hoping to not get struck by a car entering the Kennedy at Augusta Boulevard. 

Over the years, while trekking to and from school, he would observe downtown Chicago emerge as a truly modern and world-class vertical city with some office towers standing 100 stories tall by the early 1970s. Yes, he often visited downtown as a child, as his Mom worked as a clerk for Prudential Insurance during his childhood; and, his Dad would take he and his brothers to see the windows at Marshall Fields during Christmas. (You could park for free downtown back then!) This magical place, so close, reachable (you guess it) by Milwaukee Avenue, was not a place he really wanted to be part of. 

He could tell many, many stories, or better yet, recount many adventures, about times on the avenue with his buddies, guys with nicknames like Minnow, Lead Head, P-Joe, Banjo Eyes, Monster and Hutch, as they marched north toward the confluence with Division Street and Ashland Avenue. That intersection, now known as the Polish Triangle, was framed by a formidable bank building, the clothing store where he bought his first garment on layaway (a brown leather jacket) and the offices of the Polish Daily Zgoda newspaper, which his Busia read. And just west on Division Street was the YMCA, where he later learned Nelson Algren used to visit to work out with a heavy bag, then probably cavort with the gamblers, hoodlums, addicts and prostitutes who frequented the many bars to the west. On occasion, they would shoplift a small item from some modest retailer, and more than once he and a friend were mugged by older, bigger kids, toughs who demanded the few silver and copper coins he had in his pocket.  

Then there was the night—Christmas Night of 1967—when he committed theft and got caught. He, Minnow and Lead Head decided to steal some two-by-fours from the then-under construction Noble Square townhomes.  What they planned to do with the wood, he doesn’t remember, but as the trio strolled across Milwaukee at Thomas Street wood in hands, they were confronted by an unmarked Chicago Police sedan manned by two plainclothes detectives, otherwise known as “dicks.” He, the fastest by far, sped west on Thomas, but was followed by a gargantuan cop who ran faster than a man his size should be able to run in a top coat on a snowy sidewalk; for some reason, Minnow and Lead Head got away.  Yes, he was “arrested,” taken to the Wood Street station, and released to his parents.  A Christmas to really remember.

He often wondered if the wood they tried to steal was ever taken back to the construction site and used to build one of the townhomes still standing on Milwaukee Avenue.

The Roadway Today

These days, he starts his work day with a five-block regimented walk to catch the Blue Line train downtown. He navigates the same streets before reaching Kedzie Avenue and the stark Logan Square el and bus station, a scenario usually punctuated by flurry of activity from the Diversey Avenue #76 bus, pedestrians, skateboarders, cyclists of all types and the Hispanic women with kind faces who display religious literature.  Sometimes, there’s a homeless person, wrapped in rags with all possessions in a shopping cart, staking claim to a nearby storefront. Just beyond the stark plaza, with its skinny trees and Divvy station, is Milwaukee Avenue.

Before boarding the train, he can easily walk to the curb and look south. 

Gleaming glass and steel towers loom five miles in the distance, a continuance of the downtown office (and now apartment) development cycle he first observed some five decades earlier. Closer, just beyond Logan Square and all the way down to Halsted Street, developers have erected mid-rise apartment towers within the old brick structures, evidence that the corridor now helps define 21st century grit and cool for the newcomers who now inhabit this part of Chicago. 

The #56 bus still navigates Milwaukee Avenue, but bus drivers and motorists must now share the road with hordes of cyclists, helmeted commuters who’ve claimed their part of the so-called “Hipster Highway” and confidently caravan ahead on fixies. Yes, they want PBLs—protected bike lanes—but what do they pay in licensing and fees to pay for this stuff, he often asked himself.

And, the sidewalks, once a guideway for a broad demographic now is the pathway leading mostly Millennials to tattoo parlors, poke and ramen shops, vapor bars and minimalist, soulless establishments where bearded “mixologists” dispense $13 cocktails and $8 beers – and the place doesn’t even have a goddam TV!  There are still a few old-line furniture stores south of North Avenue, but those properties surely will become condos soon. Or a shared work space. These days, he often feels way out of place while walking the street he knows so well. Perhaps, he wondered: Time to grow a man bun and start that sleeve of tats?

Enough.

It’s their turn, he often said. It’s this generation’s challenge to refashion neighborhoods into the kind of environment that meets their way of living, working and enjoying life. He’ll always be able to engage in his Milwaukee Avenue, that bastard thoroughfare still pivotal, still vital, still fascinating, still part of 21st century Chicago. After all, the angled street that helped guide his life is still only a few blocks away these days.