Q: How many motorcycles did Harley Davidson build in its first year and where were they sold?

A: They sold three the first year. C.H. Lange in Chicago sold the first one; Henry Meyer of Milwaukee bought one of them; The first motorcycle that Harley sold was the so-called Silent Gray Fellow that had a single-cylinder DeDion-Bouton engine.

In 1903, William Harley and his friends Arthur and Walter Davidson launched the Harley-Davidson Motor Company. The bike had a quality engine, so it could prove itself in races, however, the company planned to manufacture it as a transport vehicle. Merchant, C. H. Lange, sold the first officially distributed Harley-Davidson in Chicago. Henry Meyer of Milwaukee, a schoolyard pal of William S. Harley and Arthur Davidson, buys one of the 1903 models
directly from the founders.

The first Harley-Davidson Dealer, C.H. Lang of Chicago, IL, opens for business and sells one of the first three production Harley-Davidson motorcycles ever made.

Three motorcycles were produced between 1903 and 1904 and were sold before they were even built. In 1903, William Harley and his friends Arthur and Walter Davidson launched the Harley-Davidson Motor Company. The bike had a quality engine, so it could prove itself in races, however, the company planned to manufacture it as a transport vehicle. Merchant, C. H. Lange, sold the first officially distributed Harley-Davidson in Chicago.
The company considers 1903 to be its year of founding, though the Harley-Davidson enterprise could be considered to have started in 1901 when William S. Harley, age 21, drew up plans for a small engine that displaced 7.07 cubic inches (116 cc) and had four-inch flywheels. The engine was designed for use in a regular pedal-bicycle frame.

Over the next two years Harley and his boyhood friend Arthur Davidson labored on their motor-bicycle using the north side machine shop 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 write off their first motor-bicycle as a valuable learning experiment.
Work was immediately begun on a new and improved machine. This first “real” Harley-Davidson motorcycle had a bigger engine of 24.74 cubic inches (405 cc) with 9-3/4 inch flywheels weighing 28 pounds. The machine’s advanced loop-frame was similar to the 1903 Milwaukee Merkel motorcycle. They also got help with their new engine from outboard motor pioneer Ole Evinrude.