Past Meetup

The City of Milwaukee's 172nd Birthday Walk Across Chicago

This Meetup is past

59 people went

Location image of event venue


Long before there was Chicago, there was a ridge of debris left behind by a retreating glacier, heading to the northwest. This ridge became an Indian trail known as the Milwaukee Trace, and then early in Chicago’s history took the name Northwestern Plank Road after it was paved with wooden planks. In 1865 an enterprising douchebag by the name of A.J. Snell bought the road, paved it with gravel, and collected tolls from anyone passing through reputedly without doing much to maintain it. Then in 1889 he was murdered in an attempted robbery by farmers disguised as Indians, and a year later the whole toll booth was burned to the ground and ever since the road has been free for all to travel. Or so the story goes, as told in various forms by historians whose memory is a bit hazy on account of not being born yet.

Thousands of other stories have been told and livelihoods made on Milwaukee Avenue along a path which really does lead up to Milwaukee, as successive waves of Germans, Scandinavians, Polish, and others settled into Chicago along this great crooked street. Some, like the Polish, migrated a bit further northwest in successive decades.


Our walking and talking group will retrace this colorful road along 12 miles, but not before a quick visit to the Leaning Tower of Niles, which is legit: a half-size replica of Pisa’s famous tower, this was originally built in 1934 as part of a recreation park for employees of the Chicago-based Ilg Hot Air Electric Ventilating Company, and was later restored in the '90s and purchased by the village of Niles in 2017. From there we'll cut west across the Forest Preserve and head into the city- Norwood Park, Jefferson Park, Irving Park, Avondale, Logan Square, Wicker Park, and West Town.

Please use Google Maps or similar to find the best way to reach the starting point from wherever you are traveling. Most will likely take the 290 bus from somewhere along Touhy or at the Cumberland Blue Line stop or the Howard Red Line station (see Because the walks are spontaneous and we encourage stopping at interesting places on the way, we don’t operate on a strict timetable once the walk begins. If you miss the beginning and want to catch up later, it’s best to connect directly with another walker you know, or estimate that we travel about 2.5 miles per hour on average. I will also encourage members of the group to volunteer to post our location on this page periodically.