CROSSING AMERICA BY CAR: A bar bet led to a history-making journey in 1903

Credit: Original article published by Barrett-Jackson.

Written by Barbara Toombs


Horatio Nelson Jackson, Sewall Crocker and their trusty companion Bud in the Winton on their epic journey across America in 1903. Photo credit: Special Collections, University of Vermont


Horatio Nelson Jackson, 1903. Photo
credit: Mary Louise Blanchard

Those of us who love our cars wouldn’t think twice about jumping behind the wheel and heading off on a road trip. But at the turn of the 20th century, it was a different story. Those newfangled horseless carriages had just appeared on the American scene in the 1890s, after all, and many considered them to be no more than a passing fad.

Not so for 31-year-old Horatio Nelson Jackson, a former physician and early enthusiast of this new mode of transportation. Such was his enthusiasm, in fact, that when a debate about the ability of the motorcar to survive a trip across America ensued at the bar of the elite University Club in San Francisco, Jackson jumped in with gusto.

The lively discussion eventually resulted in Jackson heartily accepting a $50 bet that he couldn’t make it to New York City by car in 90 days. The date was May 19, 1903.

The next four days were a whirlwind of activity for Jackson. He recruited Sewall Crocker, a 22-year-old former bicycle racer and a gasoline engine mechanic, to be his co-driver. On Crocker’s recommendation, Jackson purchased a slightly used, Cherry Red, 2-cylinder, 20-horsepower Winton touring car – one of the earliest automobiles manufactured in the U.S. – to make the perilous journey.

Sewall Crocker making repairs along the way.

The prognosis for the trip was not good, given that all previous cross-country attempts had failed. American roads were also extremely primitive at the time, with less than 150 miles paved in the entire nation. But the duo were determined. They removed the back seat of the vehicle – which they had christened “Vermont,” after Jackson’s home state – and loaded it with tools, sleeping bags, extra gas and provisions.

In the early afternoon of May 23, they chugged down San Francisco’s Market Street and set forth on an unprecedented journey. Taking note of the earlier unsuccessful routes, they headed north to Oregon before turning east. Only 15 miles outside of San Francisco, they experienced their first of many setbacks: a blown rear tire, which was replaced with the only spare.

Bud the Pitbull. Photo credit: Special Collections, University of Vermont

When they hit Idaho, the two men added a third party to the car: a pitbull named Bud, who was purchased for $15 and outfitted with a pair of goggles to keep the road dust out of his eyes.

Following bicycle paths and railroad tracks – and sometimes just venturing across open prairie – the adventurers continued their journey east, averaging just 71 miles a day initially. They overcame a broken clutch, clogged oil line, blown tires, lost equipment, running out of gas and more – relying on stagecoaches and trains to bring parts and blacksmiths to make repairs.

As they traveled, their celebrity grew. On July 12, the tenacious team arrived in Nebraska to a cheering throng. From this point onward, paved roads became more common, and they were able to gain ground, covering some 150 to 250 miles in a day. The Winton and its occupants sped through Iowa, Illinois (with a celebratory stop in Chicago), Indiana and Ohio. They finally made it to New York State – where, just outside Buffalo, they suffered their only accident, which tossed them out of the vehicle but thankfully caused minimal damage to car, man and beast.

At 4:30 a.m. on Sunday, July 26, the mud-caked Winton crawled down Manhattan’s deserted Fifth Avenue with little fanfare.

Stop along the way with welcoming crowds. Photo credit: Special Collections, University of Vermont

The journey of approximately 4,500 miles had taken 63 days, 12 hours and 30 minutes. Jackson had won his wager, but reportedly never collected the $50, which would have hardly offset the $8,000 or so he said he spent on the journey.

Jackson, his wife and Bud headed for their Vermont home on July 30, exhausted but triumphant. It is said that as the Winton crossed the threshold of the Jacksons’ stable, it let out one last sigh from its exhaust and, perhaps fittingly, its drivetrain snapped in two.

Nevertheless, the iconic American road trip had been born, and many others were to follow in their tracks from that day forward.