Let's go back to the very beginning, back to our origin. High-Wheeler, Penny Farthing, and Ordinary, all names for an iconic machine, the first to bear the name bicycle and one which sparked a revolution in recreation, transportation, and sport. Originally developed in France and England as the new United States was just picking up the pieces from the Civil War, the high-wheel bicycle didn't make its American debut until 1876 at an exhibition in Philadelphia.
By that time the more affluent of imperial Europe had nurtured an expansive bicycle culture, at the center of which was racing. Though the new machines debuted to a frenzy of interest in United States the high-wheel bicycle was already on its way out. Innovations like pneumatic tires, chain-drives, and symmetrical wheel sizes would rapidly evolve the bicycle industry as it took hold in America, eventually making a perfect platform to pair with the developing gasoline engine.
However, it is from this early era of high-wheel racing that emerged perhaps two of American motorcycle history's most important people. One, a British champion by the name of John Shilignton Prince who came to America and pioneered the development, construction, and promotion of the notorious wooden tracks known as Motordromes. The other, an American champion turned manufacturer named George M. Hendee who, with his partner Carl Oscar Hedstrom introduced the first Indian motorcycle on May 10, 1901.
This photo comes from September of 1910 during a nostalgic exhibition of the old "Ordinaries," a veteran rider H.W. Bartleet clearly at home on the cumbersome contraption in the lead.