Those Darned Diagonal Roads!

Farmers who lived in the sparsely-settled area that became Gladstone Park always had to deal with complications created by the three main roads that traveled diagonally into their area, all at different angles. While it’s true the whole City of Chicago contends with some of the same old diagonal Indian trails crossing its gridded road system, Gladstone Park in the far northwest sees the intersections in their most acute incarnations as they merge into their apexes. Indeed, N. Northwest Highway and N. Milwaukee diverge like a “V” from the community’s southwestern boundary while N. Elston careens in from the east and continues until merging with N. Milwaukee halfway up through the neighborhood. All three roads cross newer parallel and perpendicular roads at their sharpest possible angles in the most confusing of intersections. All within the span of two miles.

Aerial map with Gladstone Park outlined in blue. The three original diagonal roads are (north to south) N. Elston, N. Milwaukee, and N. Northwest Highway, all of which travel into the community at different angles. These old Indian trails, which travel as the crow flies, created confusing intersections at acute angles with parallel and perpendicular roads built later. When triangular and quadrilateral tracts of land were left in their wake, throwing whole sections of gridded blocks sideways, the small community’s future development was greatly influenced. Note that N. Northwest Highway at the extreme south along the bottom blue line is parallel to the Metra Union Pacific/Northwest Rail Line that supports its industrial corridor. A GIS (Geographic Information Systems) geospatial map from

Today each of the three main diagonal roads into Gladstone Park has a different landscape. Although the unusually wide N. Milwaukee is four-laned and N. Elston and N. Northwest Highway are both two-laned, they all have a posted speed limit of 30 mph. Each of them has also been enhanced with the 5-1/2 foot wide bike lanes Chicago has fostered throughout the city to encourage cycling. But back in the day, things were a lot different.

Milwaukee, the oldest and widest of these diagonal roads, is Gladstone Park’s four-lane main drag. Forming the community’s spine in the center, N. Milwaukee radiates a protracted 11 or so miles northwest from downtown Chicago until it enters Gladstone Park. As the community began developing, it was called “North West Plank Road” after the laying of wood planks the early 1800s to make it (more) passable in Chicago’s mud.

N. Milwaukee streetview through Gladstone Park with its four lanes and center turn lane. The central commercial corridor of the neighborhood, N. Milwaukee mixes 1920s/1930s brick and stone buildings with midcentury structures and newer strip malls of four to six or more stores. The two intersections at the extreme southern and northern ends of the community (W. Foster and W. Devon) make up the most-densely developed areas. Most of the commercial district has a profile of only one to two stories. Bigger tracts of land sport larger banks, auto repair shops, apartment buildings and funeral homes. Photo by Mina.

Recognizing its history as an old Indian trail, N. Milwaukee was later more appropriately named for an Algonquin Indian Village meaning “the land.” After the road exits the neighborhood, it continues into the northern suburbs and then runs for almost another 75 miles across the Wisconsin border to within spitting distance of that state’s capital city of Milwaukee.

The busy road…all the way from Sangamon Street in Chicago to Greenwood Road in the suburbs of Niles…has also recently been designated by Illinois as “The Milwaukee Avenue Polish Heritage Corridor” to honor the undeniable impact Polish culture has had on Chicago. Although the Polish diaspora was originally centered on N. Milwaukee in Avondale, large numbers of immigrants from that country continued to migrate north, making the city’s Gladstone Park its present-day epicenter. Indeed, Poles are still coming directly from the old country so that it is still common to hear Polish spoken on the streets of the local community today with many stores and services bilingual. At a special ceremony September 8, 2023, State Senator Robert Martwick, State Representative Lindsey LaPointe, State Treasurer Michael Frerichs, local Alderman Samantha Nugent and other officials enshrined Milwaukee Avenue with a “Polish Heritage Corridor” sign right in the heart of Gladstone Park’s Chopin Plaza.


State and local officials designating Milwaukee Avenue with a “Polish Heritage Corridor” sign at Gladstone Park’s Chopin Plaza to recognize the contributions Polish immigrants have made to the city Chicago and the local community in particular. Although the Polish diaspora was originally centered in Avondale, immigrants steadily migrated north so that Gladstone Park has become its epicenter with new arrivals still coming from the old country today. Courtesy of Nadig Newspapers, September 8, 2023

Now N. Milwaukee, running right smack dab down the center of the neighborhood, functions as its main commercial corridor with stores, restaurants, and service industries.

Although in the beginning N. Milwaukee was the main thoroughfare directly connecting Gladstone to the center city, the 10-mile long N. Elston soon gave it a run for its money. Literally…it was built as a bypass so locals wouldn’t have to pay the steep tolls charged to travel on N. Milwaukee, according to the 2017 Gladstone Park Corridor Study. N. Elston runs in a slanted line from its origins just north of Chicago’s Loop to near the northern edge of the community to where it unceremoniously ends when it bumps into N. Milwaukee.

People today get a kick out of hearing that N. Elston, generically known then as “Lower [Plank] Road,” was considered so far out from the city in the mid-1800s that it was said to be at “the northern limits of civilization,” according to Don Hayner and Tom McNamee in Streetwise Chicago: A History of Street Names. The roadway was later named for one of its original residents: Daniel Elston, bank owner, brickyard operator, real estate investor, and Chicago Alderman in the 1840s/1850s when there were only a handful of city councilmen.

The section of N. Elston that runs through the neighborhood serves as home to many two-flats, a smattering of apartment buildings and single family homes with the occasional dental or real estate office, auto repair shop, daycare, or small pub mixed in.

N. Elston streetview through Gladstone Park showing an apartment building, a few single family homes and the many two-flats that make up its landscape; the occasional small office, auto repair shop, daycare, and small pub is found on some corners or in designated blocks. Photo by Mina.

Northwest Highway, named for its directional slant, now forms much of Gladstone Park’s western boundary, depending who you ask. Like N. Milwaukee, it is also an old Indian trail. Oddly, it starts near the neighborhood’s southern border near W. Foster before continuing straight into the Norwood Park neighborhood to its west before passing through the city limits into the northern suburbs.

Northwest Highway at the western edge, bordering on the Metra Union Pacific/Northwest Rail Line, is the community’s light industrial corridor. It hosts a conglomeration of everything from metal fabricators to car washes to small restaurants to electric component manufacturers to a firewood supplier and a bowling alley.

N. Northwest Highway Streetview through Gladstone Park shows the small, low rise industrial corridor located on the southwestern border of the community backing right onto Metra’s Union Pacific/Northwest Rail Line. Note the one-story character of many of the small manufacturing and service concerns. Within blocks are two entry ramps onto the John F. Kennedy Expressway: one toward the center city of Chicago and all points east, the other traveling the 4-1/2 miles to O’Hare Airport and all points west. Photo by Mina.