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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It all started after Chicago annexed the greater Jefferson Park neighborhood in 1889 along with Gladstone Park to its north. Problem was, the city had to contend with new roads sprouting up all over that intersected with three old Indian trails practically on a collision course with each other as they travelled diagonally through the community at different angles. When the Plan of Chicago firmly established its systematic arrangement of urban streets within its rectangular grid system in 1909, these new streets had to somehow fit within the three original main roads that forced their way into the neighborhood on the slant. Learn More…

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 system 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…

Broken Roads, Boulevards & No Roads At All
There are 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. But these oddities are what contribute to making Gladstone Park both special and unique. Learn More…

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 lots. Developers and builders were forced to come up with various schemes as to how to alter the architecture and/or siting of homes and commercial buildings to fit on these non-rectangular lots and still have some sort of front and back yard for each. Learn More…

To ease driving and promote safety, Chicago was pressed to post inventive street signs to direct Gladstonians and its visitors to help them get where they were aiming to go. Yeah, your car’s GPS navigation apps can help. 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…

Still, Gladstone Parkers celebrate their roadways as home to four official commemorative streets. Three of these streets honor people, as is typical, but the community is the only one in all of Chicago to boost a commemorative street that celebrates a famous hot dog restaurant. Learn More…

Gladstone Park’s Road Rebellions!
With the populace’s very survival depending so heavily on its roadways, it’s no surprise that Gladstone Park 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 10 years ago, 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.