We’re big fans of racing. All sorts of racing. One of the first Automobile races in America was in Chicago Illinois in 1895. It was called the Chicago Times-Herald race. Originally it was to take place from Chicago to Milwaukee, but the roads at the time were so terrible that nobody thought that the cars would make it. So it was redone to be from Chicago to Evanston and back, ending near what is now the Museum of Science and Industry.
There was 83 cars signed up for the race, but only 6 arrived to actually compete. After some initial issues with ordinances and police. The race was put on Thanksgiving Day, Nov 28th, 1895. The 54 Mile race would take the cars or “Moto-Cycles” as they were coined in the paper, The race would take them up the Lake Michigan coastline to Evanston, there they traveled inland a bit. Then make their way south and then go through Downtown Chicago. Charles Duryea won the race in his “Motorized Wagon”.