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America’s First Cross-Country Road Trip In 1903, automobiles were still new and unreliable, and most Americans doubted a car could cross the country. In San Francisco, a young doctor named Horatio Nelson Jackson made a $50 bet that he could drive to New York City. Jackson bought a used Winton touring car and set out with mechanic Sewall K. Crocker and a bulldog named Bud. The trip was difficult — they traveled on rough wagon roads, faced constant breakdowns, and sometimes followed railroad track
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