Organized Chaos: Gladstone Park’s Tangled Streets

They say whatever doesn’t kill you will make you stronger. In Gladstone Park that whatever is its streets. They are the one element that shaped this Far Northwestern Chicago neighborhood more than any other.

Home to some of the nuttiest road geography in the city, Gladstonians here take their streets very seriously. They’ve had to ever since the mid-1800s when the neighborhood’s roadways were the infrastructure that fueled the area’s economy by providing the pathways for farmers and merchants to bring their goods to market in the center city.

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Aerial map of Gladstone Park

Those Darned Diagonal Roads!

It all started after Chicago annexed the greater Jefferson Park neighborhood in 1889 along with the Gladstone Park community to its north and had to contend with new roads sprouting up that intersected with the parallel and perpendicular thoroughfares that were already there. Problem was, the new streets had to cross three old Indian trails that travelled in diagonally at different angles in very close proximity to one another. When the Plan of Chicago firmly established its systematic arrangement of urban streets within its rectangular grid system in 1909, the new streets had to somehow fit with the neighborhood’s three original main roads that travelled in on the slant. Learn More…


Street Signs at Angles

Gladstone Park’s “M” Streets

With the ordering of north/south streets based on an alphabetical naming system starting at Lake Michigan, the Plan of Chicago gave the community identification and order by assigning “M” avenues when it got to Gladstone Park, having exhausted “A” through “N” in neighborhoods further east. Its directional numbering component meant that houses here were assigned numbers from 5200 in the south to 6300 in the north, representing how far they were from the center city. Learn More…


Boulevard Street

Broken Roads, Boulevards & No Roads At All

While there may be many oddities in Gladstone Park’s street structure — broken roads, houses not on physical streets at all, a boulevard stuck in the middle of nowhere — these oddities contribute to what make Gladstone Park special. Learn More…


Angled commercial building

Triangular- & Quadrilateral-Shaped Lots

The creation of so many irregularly-shaped commercial and residential lots was unavoidable when the city overlayed its straight road grid across slanted streets in such a small area of only one square mile. It resulted in intersections of three or more roads at acute angles, sections of rectangular blocks thrown sideways, and triangular and oddly-shaped quadrilateral tracts of land. Builders were forced to come up with various schemes as to how to alter the architecture and/or siting of homes and commercial buildings on these non-rectangular lots. Learn More…


Milwaukee Ardmore Austin Light

Street Signs & Traffic Lights

To ease driving and promote safety, Chicago was pressed to post inventive street signs to direct Gladstonians and particularly its visitors to help get them where they were aiming to go. Nevertheless, it is easy to take one wrong turn in the community, lose a complete sense of direction on the angled roads, and end up driving in circles, fully lost. And that’s after going through adventurous, if not torturous, traffic lights to get into the neighborhood in the first place. Learn More…


Superdawg (Honorary) street sign

Honorary Streets

Still, Gladstone Park can have fun with its roadways, becoming home to four commemorative streets honoring people and, in one case, a famous hot dog restaurant. Learn More…


treed median

Gladstone Park’s Road Rebellions!

But with the populace’s very survival depending so heavily on its roadways, it’s no surprise that it developed a long history of fighting for its streets. Whether it was tearing down tollbooths 130 years ago, protesting a superhighway 60 years ago, or defending the width of its main Milwaukee Avenue thoroughfare during the last 10 years, Gladstonians have guarded their streets with their lives. Learn More…


Through it all, the neighborhood grew under its streets’ constraints, creating its own little world surrounded by an environment of natural beauty. The result is that virtually no one in Gladstone Park is more than three or four long blocks from a neighborhood park or the hiking trails, cycling paths, and golf course in the expansive Forest Preserves on its entire northern border.

This section explains how the community managed to do it all.

Click here to continue to the next section: Those Darned Diagonal Roads!