At 6 a.m. on August 10th, 1909, from in front of Cleveland’s Hollenden Hotel, 96 enthusiasts from America’s heartland set off on a grueling endurance run. The 362-mile adventure was to terminate in Indianapolis on August 12th in conjunction with the grand opening of the newly constructed Indianapolis Motor Speedway, and as such made for a staggering level of interest and fanfare. It was reported that the citizens along the route retired from their daily duties, making an unofficial two day, midweek holiday. Every city along the way set up a grand reception with bands, parties, and performances, while the farmers and their families lined the dusty country roads, watermelon patches, and front porches along the way. Of the 96 men to leave the starting line only 29 were private owners, the remainder represented a growing interest from manufacturers themselves in fielding teams for such competitions. Eighteen brands made up the field, from the established Curtiss, Yale, and Reliance, to the newcomers like Pierce, New Era, and Marvel, and of course the ever-present Indian, Merkel, and relatively new Excelsior and Thor. Among the entrants were motorcycle culture pioneers like Oscar Hedstrom, Albert Crocker, and Cannonball Baker, as well as eventual superstars of the American motordrome Arthur Chapple, Don Klark, and William Tuebner. In total 37 men crossed the finish line with a perfect score of 1,000 points, having made their daily checkpoints on time and never having dropped a foot on the multiple hill climbs along the way.
Posing in front the Cadillac Company of Indiana’s storefront at 25 E. Ohio St. in Indianapolis, this group made up four of the seven entries who piloted machines from a relatively young motorcycle company from Milwaukee, Harley-Davidson. Though their origins are claimed to have been 6 years prior, the Harley-Davidson Motor Company had only just incorporated and began scaling up production less than 2 years before this photo was taken. Officially, Harley-Davidson wouldn’t enter into the high stakes game of professional factory racing until the last days of 1914, but in these early days many of the company’s original employees, as well as devoted early adopters of the manufacturer could be found on the starting line of endurance competitions and hill climbs. Only 3 of these men pictured represented the factory effort, two of which, Frank Ollerman and S. Lacy Crolius were among the original handful of employees hired in 1907, the other being co-founder Walter Davidson who was an avid competitor. Ollerman was a German immigrant who was an essential figure in the early days of the company, occupying any role that needed filling and earning numerous awards and accolades as a consistent face in early competitions. S. Lacy Crolius was initially brought on as a drill press operator, but in 1910 was made the head of the company's in-house advertising department, an essential role in a rapidly expanding company.
Chicago’s R.E. Underhill rounds out this group but was actually competing as a privateer along with the remaining 3 Harley-Davidson riders that are not pictured. Every man who entered onboard a Harley-Davidson earned a perfect score for the 362 mile trip to Indianapolis, with the exception of a local Cleveland man named Andrew Davies. Davies dropped out just before hitting the 100-mile mark on the first day, but it wasn’t his machine that bore the responsibility for his retirement. Davies had only taken up riding a few weeks prior and somewhat boldly assumed that he could make the trek with no trouble it all. Crippled with back pain after such a jarring affair, Davies pulled off and was claiming an issue with his exhaust valve, but after hitching a ride and finding nothing wrong with the machine it was later reported that Davies had “left his backbone somewhere along the route.” Nevertheless, Harley-Davidson was quick to capitalize on their strong showing at yet another endurance competition and had a number of full-page advertisements running across the country within days. From left to right, a crew of Renault Grey and Khaki with drive belts to spare are R.E. Underhill, Frank Ollerman, S. Lacy Crolius, and Walter Davidson on one fine summer evening in Indianapolis, August 12th, 1909.