Horatio Nelson Jackson’s journey in 1903 wasn’t just a cross-country drive; it was a testament to the grit, vision, and sense of adventure that defined America’s early automotive pioneers. He was a man of many talents—doctor, Medal of Honor recipient, and a visionary who saw the automobile as more than a novelty. At a time when cars were expensive, unreliable curiosities for the rich, Jackson believed the automobile would one day shape the world in ways few could imagine.
It all started on a whim in San Francisco. During a visit to the University Club, Jackson took on a $50 bet (worth about $1,300 today) to drive a car across the United States—a feat never accomplished. The challenge was audacious. Jackson didn’t even own a car and had little experience behind the wheel. But when he saw his wife off at the train station for their return trip to Vermont, he committed to the journey.
Jackson sought a companion and found the perfect partner in Sewall Crocker, a young mechanic and chauffeur with a practical understanding of automobiles. Crocker recommended they buy a Winton, a solid choice among the limited options in 1903. The 20-horsepower Winton, affectionately named “The Vermont,” became their makeshift expedition vehicle. With a basic toolkit, limited spares, and a small cache of supplies, they set out on May 23.
The Winton wasn’t built for rugged terrain, and their journey was one of frequent breakdowns and roadblocks. The first tire blowout happened just 15 miles in, quickly revealing how scarce automotive supplies were. They barely found one spare tire in San Francisco and resorted to using lanterns ill-suited for open-road night driving. Near Sacramento, they scrounged for inner tubes but remained without additional tires—an oversight that would later lead to some clever improvisation with rope.
Misadventures abounded. Somewhere between Sacramento and Oregon, their cookware fell off. A woman deliberately misdirected them so her family could see an automobile, a detour adding 108 miles to their trip. When more tires failed, they wound rope around the wheels until they reached a telegraph office to wire for replacements, waiting in Alturas, California, for tires that never arrived. Forced to press on with their rope tires, they eventually floated the car across streams with a block and tackle as they traversed the Oregon Trail.
Every few hundred miles, the Winton needed repairs, often with whatever parts they could scavenge or borrow. In one instance, after a breakdown in rural Oregon, a cowboy towed them to a ranch. When they found their gasoline had leaked away, Jackson rented a bicycle, pedaling 25 miles to Burns, Oregon, to refill their fuel supply. After nearly two weeks, they had only made it 352 miles, a trip that today would be just a six-hour drive.
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| Bud |
Their journey took a turn for the better—or at least more adventurous—when they acquired Bud, a Pit Bull with a big personality. Legend has it that Jackson bought him for $15, though local newspapers spun colorful tales about Bud’s acquisition. Bud became a symbol of their adventure, complete with his own set of goggles to shield his eyes from the dust—a necessity on the rough, dusty roads they traveled.
The challenges continued. Near Idaho, Jackson lost his coat with nearly all their funds. In need, he wired his wife, who sent money to Cheyenne, Wyoming. Each day seemed to bring a new challenge, from sourcing parts like a wheel bearing from a farmer’s mower to hunting down gasoline in remote areas.
On July 12, they reached Omaha, Nebraska, a milestone that meant smoother roads and more settled areas ahead. Modern roads with stretches of pavement made the final leg of the trip feel easier, though the adventure wasn’t over. They reached New York City on July 26, after 800 gallons of fuel, a lot of ingenuity, and two months on the road. Jackson’s wife met him there, and together, they drove back to Vermont. Fifteen miles from home, the Winton broke down yet again. A family reunion rescue mission turned comical when both the rescue car and the Winton broke down, leading Jackson to tow everyone home.
Jackson’s journey marked the first successful transcontinental car trip, a pioneering feat that helped prove the automobile’s potential to transform daily life and long-distance travel. By taking on the open road—and all the unknowns it held—Horatio Nelson Jackson became an icon of American automotive history, paving the way for a century of cross-country road trips and automotive dreams.
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