芝加哥先驅報 (Chicago Times Herald) 贊助這場比賽，冠軍可以贏得2000美金，而把這種無馬運輸工具取名為摩托車的人則獲得500美元的獎金。 

不過在更早的兩年前，法蘭克‧杜伊爾和他的兄弟查爾斯 (Charles Duryeas) 就已經建好並駕駛他們認為是美國第一輛以石油當作動力的汽車。不過在先驅報舉辦這場徵名比賽的時候，已經有超過70個人報名參加了。 因為大眾熱烈的迴響，使得克裡夫蘭總統要求戰爭部要重視這個事件。在杜伊爾獲得勝利之後，兄弟二人打造了13部同型的芝加哥汽車，而法蘭克‧杜伊爾又打造了一輛昂貴的汽車，稱之為史帝文斯‧杜伊爾 (Stevens-Duryeas) ，一直到1920年代都還有生產。

The Chicago Times Herald sponsored that first race with $2,000 going to the winner and $500 to the fan who named the horseless vehicles "motocycles."

Two years earlier, the winners, J. Frank Duryea and his brother Charles, had built and driven what they claimed to be the first American gasoline-powered automobile. Yet by the time the Times Herald race came along, more than 70 entries were filed. This huge response prompted President Cleveland to ask the War Department to oversee the event. After their victory, the Duryeas made 13 copies of the Chicago car, and J. Frank Duryea developed the Stevens-Duryea, an expensive limousine that remained in production into the 1920s.

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