From the very beginning of their enterprise, the intent of the Davidsons' and William Harley was to build a rugged, dependable motorcycle that was suitable for personal transportation.  To this end, they continued to produce slightly improved versions of their original model.  In 1908, the year that Indian cataloged a chain-drive, two-cylinder production racer, Harley-Davidson was still selling an improved version of the first belt-drive, motor-driven bicycle that they had belaboredly constructed in 1903.

Until the summer of 1908, the H-D Company ignored all types of competition.  A number of their bikes, however, were entered in various endurance or economy events by private enthusiasts, but when Harley-Davidsons did succeed it was generally due to their inherent ruggedness and dependability, never their speed.

Finally, Walter Davidson, President of the company, decided that H-D could no longer afford to ignore competition, especially in light of the publicity that the other factories were getting by boasting of their racing success.  Consequently, in June of 1908, Davidson personally entered an endurance competition held in New York.  When the results were tabulated the 32 year-old executive had scored a perfect 1000 points.

The following weekend Walter entered an Economy Run held on Long Island.  Once again, the president of the Milwaukee company racked up a sensational victory as it was calculated that his machine had achieved 188 miles to the gallon of fuel!  Within a short time established dealers reported increased sales as a result of the publicity that followed Walter's success.  Still, the Harley-Davidson company had a lot of catching up to do.

That same year, Bill Harley returned to the factory from the university in Madison where he had earned a degree in automotive engineering.  Upon his return, the graduate engineer's first assignment was to design an updated, more powerful version of the H-D single as well as a prototype twin.

The updated single was introduced for the 1909 sales season, but the 28 year-old engineer had teething problems with the twin and it took until 1911 before the first H-D twin was ready to be sold to the public.  By this time all racing machines utilized a chain drive as the means to transmit power to the rear wheel.  Following the lead of the other major manufacturers, Harley-Davidson finally cataloged a chain-driven motorcycle toward the end of the 1912 sales season.

While the H-D factory still declined to support an "official" racing effort, or for that matter to provide private owners with financial or technical help in their racing endeavors, Harley-Davidsons entered by privateers continued to make laudable showings in some of the well-publicized road races of the day.  These so called "road races" were in effect endurance contests often conducted over unimaginably difficult terrain.

The most arduous was the 421-mile San Diego to Phoenix, Arizona road race first held in 1913.  Known as the nation's most punishing and brutal race, riders gambled with sand, rock slides, dry washes, sun-stroke, wrecks, trigger-happy Mexican bandits (the race was called off in 1915 because of raids by Pancho Villa along the race route), and renegade Apache Indians on the prowl.

Readers of the trade press were thrilled by accounts of riders who, after losing their machines in the deep sand of the forlorn desert, were relegated to wander for hours, suffering from thirst and sand-clogged boots.  Harley-Davidsons, entered by privateers, finished 7th and 8th in the 1913 race with the result that the Milwaukee manufacturer received more favorable publicity.