On July 9 1895 the Chicago Times-Herald took a cue from the French to announce a race for motor vehicles, the first in the USA, “A Prize for Motors”. The world’s first motor vehicle race had been held only a year prior, running from Paris to Rouen, and imports of the first production automobiles had only reached the USA in 1893. Motorized carriages were considered a passing fad, but H.H. Hohlsaat, publisher of the Times-Herald, was a far-sighted fellow, and wanted to promote the nascent industry of motoring. He lured entrants to his contest with a $5000 prize for “inventors who can construct practicable, self-propelling road carriages.” The course was a 54-mile route from Chicago to Evanston, and back.The Chicago Times-Herald Race of 1895



“We think that this new means of transportation is destined to play an important part in the question of city traffic,” – Scientific American
The notorious flim-flam man E.J. Pennington arrived with two vehicles: the two-wheeled ‘motorcycle’ (as he called his motorized two-wheelers, becoming the first to do so, in 1893) with which he eventually fleeced investors, and a larger vehicle made by doubling up his motorcycle. Interestingly, the Pennington machines were one of only two vehicles using rubber balloon tires recently invented by John Dunlop (1888), which everyone admired for their greater ability to handle the slush, and the smooth ride they provided compared to the solid tires of every other vehicle.



From Scientific American, Dec. 7 1895:
“It was extremely unfortunate that the weather should have interfered so seriously with the Chicago Times-Herald motocycle contest, which came off at that city on Thanksgiving Day. The recent storm had left the roads heavy with snow and mud. We are told that for miles on the west side the boulevards were unbroken fields of snowbanks and slush. Six machines lined up for the start : The Duryea, of Springfield, Mass.; the Morris & Salom Electrobat, of Philadelphia; the H. Mueller motocycle, of Decatur, Ill, the R. H. Macy, of New York; the De la Vergne. of New York ; and the Sturges electric motocycle, of Chicago. The Roger motocycle, with a view to giving it a long distance test. was started from New York to Chicago by road on November 15; but it was stalled by snow when it reached Schenectady.






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