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.

Click on any heading below to learn more about that topic.

Aerial map of Gladstone Park

Those Darned Diagonal Roads!

It all started after Chicago annexed the greater Jefferson Park community in 1889 and the Gladstone Park section in the north had to contend with new parallel and perpendicular thoroughfares being built into its neighborhood. 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 with its rectangular grid system in 1909, the new streets had to hack over through the neighborhood’s three original main roads that came in on the slant…as the crow flies. Learn More…

Street Signs at Angles

Gladstone Park’s “M” Streets

But the city’s Plan also gave the community identification and order in its “M” north-south streets and addresses based on a directional numbering system. All its houses 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

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

Angled commercial building

Triangular- & Quadrilateral-Shaped Lots

It all goes back to how astronomical an impact resulted from overlaying so many straight roads across slanted streets in such a small area of only one square mile. There were intersections of three or more roads at acute angles, sections of gridded 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 the non-rectangular lots. Learn More…

Milwaukee Ardmore Austin Light

Street Signs & Traffic Lights

To help the situation, Chicago was pressed to post inventive street signs to direct Gladstonians and particularly its visitors to where they were aiming to go. Nevertheless, it is easy to take one wrong turn 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 the main thoroughfare during the last 10 years, Gladstonians have guarded their streets with their lives. Learn More…

Through it all, the neighborhood grew stubbornly under its streets’ constraints, creating its own 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 the golf course of the expansive Forest Preserves on its entire northern border.

This section explains how they managed to do it all.

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