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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This is an excellent article with photographs I had not seen in my own extensive research into the Chicago Times-Herald Race.
There is some confusion with the word “motocycle” used in the write-up. It does not indicate motorcycles were in the race, in fact, no two-wheeled vehicles were qualified to enter. The Chicago Times-Herald had held a contest to determine what these new-fangled vehicles should be called. The term “moto-cycles” was declared the winner. I believe the Times-Herald always hyphenated the word which would help delineate the difference from the modern motorcycle.
It would be inappropriate to criticize such a fine article but the term appears too frequently and attracted my attention.
I would like to say that any vehicle with the name Pennington attached is suspect as to its functionality. E.J. Pennington is the PT Barnum of early automobiles and he seemed to have left financial ruin in places which he soon left. None of his partners appear to have benefitted from his grandiose ideas and claims.
I repeat for a third time, the article on the 1895 Race is terrific! I hope is that my comments will make it more clear and more fun.
Hi Alex,
actually, the term ‘motocycle’ was coined to include ALL motorized vehicles, including motorcycles. Indian used the term ‘motocycle’ officially until the mid-1920s.
You are correct that no motorcycle was considered suitable for the race per se, but several were entered, and are thus of interest, since they are so strange! And you’re absolutely correct about Pennington, the original swindler!