Spectators line the street in front of the Borman Shoe store, 4806 N. Milwaukee Ave., as bicyclists race past during the Memorial Day Road Race of 1897. View Full Caption Northwest Chicago Historical Society

CHICAGO — Starting in 1886, cyclists gathered every Memorial Day for a 25-mile competitive bike race along Milwaukee Avenue, leading from northwest suburban Wheeling down to the city's West Side.

And the avenue — which today funnels thousands of two-wheeled commuters each day — wasn't such friendly terrain for bicycles in the 19th century.

Northwest Chicago Historical Society board member Frank Suerth explains:

Milwaukee Avenue [was] not the Milwaukee Avenue that one knows of today but a dirt road with ruts and other obstacles. Just a half-mile from the start of the race, riders had to “narrow down” for the bridge over the creek flowing into the Des Plaines River. Riders unable to “narrow down” due to the crowded participants on the bridge made a wet detour. The course for the road race ... would start at the Wisconsin Central Station, one mile west of the Wheeling Town Hall, east to Milwaukee Avenue, then south down Milwaukee through Niles, Jefferson Park and Logan Square, south from there to Palmer Square, east to Humboldt Park, through the park, south and west on Central Park west, to Garfield Park, through the park to Madison Avenue and finishing at Jackson Blvd in Garfield Park, a distance of almost 25 miles. As the years passed, the riders and spectators that lined the roads grew, therefore in 1897 handicaps were given, age and ability were taken into account. That year also saw two bicycle organizations hold two races the same day both starting from Wheeling. The higher the handicap the earlier the starting time, thus staggering the starting times for both races. Many cyclists had a difficult time near Jefferson Park because portions of the road had been repaired with coarse gravel and in one place a mile north, there was a path only two feet wide fit for cycling. Cyclists needed to travel single file through this section. Many racers displayed torn numbers and tattered clothing with bruised noses; these were the ones that did not drop out of the race because of their injuries.

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