In 1901, William S. Harley, age 21, drew up plans for a small engine with a displacement of 7.07 cubic inches (116 cc) and four-inch (102 mm) flywheels. The engine was designed for use in a regular pedal-bicycle frame. Over the next two years Harley and his childhood friend Arthur Davidson labored on their motor-bicycle using the northside Milwaukee machine shop at the home of their friend, Henry Melk. It was finished in 1903 with the help of Arthur's brother, Walter Davidson. Upon completion the boys found their power-cycle unable to conquer Milwaukee's modest hills without pedal assistance. Will Harley and the Davidsons quickly wrote off their first motor-bicycle as a valuable learning experiment.^[7]

Work immediately began on a new and improved second-generation machine. This first "real" Harley-Davidson motorcycle had a bigger engine of 24.74 cubic inches (405 cc) with 9.75 inches (25 cm) flywheels weighing 28 lb (13 kg). The machine's advanced loop-frame pattern was similar to the 1903 Milwaukee Merkel motorcycle (designed by Joseph Merkel, later of Flying Merkel fame). The bigger engine and loop-frame design took it out of the motorized-bicycle category and would help define what a modern motorcycle should contain in the years to come. The boys also received help with their bigger engine from outboard motor pioneer Ole Evinrude, who was then building gas engines of his own design for automotive use on Milwaukee's Lake Street.

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