The goal: Drive from San Diego to New York City in the shortest time possible.
The challenge: Everything in between.
The rules: None.
The first individual to accomplish the above was none other than Edwin “Cannonball” Baker. He completed his infamous dash in 1914, half a century before the Interstate Highway System, on a motorcycle in 11 days. It was a journey that set the course of his life, earned him his nickname, and awestruck a nation.
The story begins two years earlier in Indianapolis, where Baker worked as a machinist and got involved in some of the first motorized bicycles. He was approached by co-founder of the Indian Motorcycle Manufacturing Company, George Hendee, to take one of his company’s two-speed, seven-horsepower models on a demonstration tour through Cuba and Central America. After 14,000 miles and three months later, Baker finished in Panama and boarded a steamer up to San Diego.
Instead of going back to Indianapolis from San Diego, Baker stayed around for a while and competed in several endurance runs in California and Arizona during this time. It was all preparation for what was to be the grandest race of his life. In 1914, after careful preparation and an iron will, Baker mounted his pure stock Indian V-Twin motorcycle and set out on a cross-country race against time.
He faced treacherous weather, rabid dogs, flat tires, and seemingly unpassable terrain (he once spent a whole day trying to find a suitable place to cross a river!) and still completed his epic ride. Upon arriving in the Big Apple, newspaper reporters swarmed to ask questions and one reporter compared him to the Cannonball Express train of the Illinois Central railroad. The name stuck. “Cannonball” Baker would go on to set 143 driving records from the 1910s through 1930s, driving not just motorcycles but vehicles as varied as the Model T, a fully-loaded two-ton truck, and a Cadillac 8 roadster. “No record, no money” he would tell his sponsors. He once raced a 20th Century Limited train in a race from New York to Chicago and won.

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