Behind a pair of non-descript black doors, to the left of the main entrance to 100 W. Monroe, lies a mostly-forgotten remnant of Chicago's pastoral past. In 1844, Willard Jones, the owner of a 90-foot-wide parcel of land to the northwest of Clark and Monroe, sold almost the entire southern portion of the lot to Royal Barnes. Jones retained a 10-foot wide pathway on the western side of the lot to ensure he had a route by which to take his cows from his remaining parcel north of Barnes' property through to Monroe Street and then on to a pasture near where the Board of Trade now stands. A couple of years later, Jones sold the northern lot to Abner Henderson, but included in Henderson's title the right to use the cowpath abutting Barnes' land.

Decades passed and the cowpath remained, growing ever more obsolete as skyscrapers replaced farms and fields. Its existence resurfaced in the news in 1927 when the owners of the Barnes parcel tried to construct a new building at 100 W. Monroe but the owners of the Henderson lot insisted on keeping their right of way to the cowpath. The court ruled in favor of keeping the cowpath, forcing the developers at 100 W. Monroe to build over it, resulting in a building with a first floor ten feet narrower than the floors above.

At some point not long after, First National bank built an annex to the north of 100 W. Monroe, cutting the cowpath short. It still exists in the tunnel next to 100 W. Monroe, but any cows using it to cut through to Madison will have to find another route.

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