When you're in the loop, you expect to see the usual stuff: office buildings, elevated tracks, restaurants, bars, busy commuters/tourists/residents enjoying the downtown ambiance, and even the occasional indigent individual. One thing you wouldn't expect to see are cows(well, except for that one time in 1999). And you're right, there are no cows on the city. But there is a cow path.
It all goes back to those days far in the past(before the city was even incorporated) when Chicago was just a glorified frontier village with a Fort. People started coning to the city in droves, and a development boom kicked off. Suddenly properties in the future area of the Loop were being snapped up like hotcakes. By the time 1844 came around, the market was in full boom mode. This was when local farmer Willard Jones decided to take a piece of the action for himself, and began selling off parcels of his land. However, he needed to look out for his cattle and still ensure a clear route to take them to pasture. So in all the deals he made, he included an easement that provided for a clear path to bring the cattle back and forth. Chicago boomed, Chicago burned, and Chicago rose from the ashes. Old Farmer Jones stayed loyal to his cattle until he eventually passed on. The 20th Century dawned and the Loop was certainly no place to be raising cattle anymore. But in 1925, the Illinois Supreme Court ruled that Jones' easement was still a legally binding contract which developers had to respect.
To this day, you can still see evidence of a cow path in the Loop if you know where to look. It may be an unusually large alley, an out of place gap in the buildings, or even a locked black door in the middle of a row of shops, as can be seen at 100 W. Monroe. Over the years, the Illinois Livestock Exposition would periodically bring cows to this area for photo ops, startling office workers in the area. A sign that used to mark the path disappeared several years ago, but the evidence is still there, providing yet another link to Chicago's frontier past.
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