At the beginning of any cross-country road trip, it is only right to recognize the first person who drove a car across the United States: Horatio Nelson Jackson. That’s him at the top, driving the Winton Motor Carriage Company automobile he used to make the trip.
He did it to win a $50 bet made at San Francisco’s University Club in 1903. At the time he didn’t own a car and had little driving experience. Even so, he suspected that the lack of paved roads, especially in the western parts of the country, might prove difficult, so he hired a mechanic, Sewall K. Crocker, to travel with him. They set out from San Francisco on May 23, 1903.
They passed through Sacramento (Route 50′s current western end) and then veered north, in part because attempts by others had foundered in the deserts of Nevada and Utah. For guidance, Jackson borrowed maps from bicyclists he met along the way.
Challenges encountered and overcome included flat tires, car breakdowns, cooking gear falling (unnoticed) off the car, the need to cross streams using a block and tackle, lost money, and near starvation.
Jackson was consoled on the journey by the presence of his dog, Bud, who wore goggles because the dust from unpaved roads bothered his eyes. Driver, mechanic, and dog reached New York City on July 26, 1903, sixty-three days after leaving San Francisco.
Horatio Nelson Jackson then resumed his career as a successful businessman. His car, which he named “The Vermont” after his home state, is now in the Smithsonian Institution.

Photos of Horatio in the Vermont and his dog Bud are in the public domain and not copyrighted.