America's First Road Trip: How a $50 Bet and a Dog Got a Nation on the Move

Ur-Turn
by Ur-Turn

by Richard A. Ratay

The first noteworthy attempt to drive across America began as many ill-advised feats do — on a bet. While visiting California in 1903, a 31-year old doctor named Horatio Jackson accepted a friend’s invitation to join him for a drink at San Francisco’s University Club.

It’s there, over a cocktail — or likely several — that Jackson found himself in debate with another gentleman on the topic of whether automobiles, then just beginning to appear on city streets, were merely a passing fad. An enthusiastic admirer of the new contraptions, Jackson passionately argued that cars were nothing less than the future of transportation.

In fact, Jackson boldly asserted, automobiles were already so rugged and reliable he could drive a car clear across the country back to his home in Vermont.

Perhaps to his chagrin, Jackson’s declaration was immediately challenged and a wager was set: $50, about $1200 in today’s money. Jackson wasn’t fazed by the amount; he was wealthy. Nor apparently was he dissuaded by the fact that he didn’t own a car, had barely driven one, or that scarcely any roads existed west of the Mississippi River. But he may have regretted having to explain his bet to his young wife the following morning. Rather than joining her husband on the adventure, she opted to take a train home instead.

Undaunted, Jackson prepared for his epic journey. He hired a young mechanic, Sewall Crocker, to serve as his backup driver and traveling companion. On Crocker’s advice, Jackson purchased a two-cylinder, 20-horsepower Winton touring car. With perhaps a touch of inflated optimism, Jackson named the car Vermont, after his home state and the destination he hoped to reach.

Together, Jackson and Crocker planned a route heading north along the California coast before proceeding east along the Oregon Trail. Their aim was to avoid the treacherous Rocky Mountains and baking deserts of the Southwest that had doomed earlier attempts to cross the country by car.

The pair then loaded their Winton with all manner of gear: sleeping bags, blankets, canteens, overcoats, watertight rubber suits, a water bag, axe, shovel, telescope, tools, spare parts, cans for extra gasoline and oil, rifle, shotgun, pistols, and a pulley system they could use to extricate themselves should they become stuck in mud. Last but not least, they bought an Eastman Kodak camera to document their adventure. On May 23, 1903, Jackson kissed his exasperated wife goodbye and he and Crocker set off.

Things didn’t start smoothly. Not even 15 miles into their journey, the duo’s car blew a tire. On the second night, the men realized the Winton’s side lanterns weren’t nearly bright enough to light their way after dark, and they were forced to purchase a large spotlight to mount on the front grill.

Days later, Jackson and Crocker failed to hear their cooking equipment fall off over the din of the car’s engine. Near Sacramento, the pair was given bad directions—on purpose—by a woman because she wanted her family to get their first look at an automobile. The detour added 108 miles to their route. In Oregon, the pair suffered two more flats. Lacking spares, they wound thick rope around the wheels as a makeshift substitute until they could find new tires.

Not long afterward, they ran out of fuel. Jackson was forced to rent a bicycle and pedal 25 miles to a town to purchase gas then ride back with four heavy cans strapped to his back. Along the way, the bicycle also blew a tire. All this before the twosome had even really left the West Coast behind.

By the time Jackson and Crocker reached Idaho, news of their quest was beginning to spread. Their fame was bolstered by Jackson’s decision to pick up another traveling companion — a spunky pitbull named Bud.

While driving across the arid salt flats of Utah, the dog’s eyes became so irritated by dust kicked up by the car’s tires that Jackson had Bud fitted for his own driving goggles. The press ate it up, turning out to take pictures and conduct interviews with the trio at every stop. Jackson, Crocker and Bud became national celebrities.

After reaching Nebraska, the quality of the roads improved and so did the adventurers’ luck. Finally, on July 26, 1903, after 63 days on the road (and off it), the Vermont and its exhausted crew rolled onto the streets of New York City, completing the first successful crossing of the North American continent by automobile.

So, the next time you load up your SUV, get the kids situated in the backseat with their iPads, and set off on smoothly paved interstates following a route carefully planned by your GPS navigation system to some distant destination, remember to tip your cap to Jackson, Crocker and Bud. After all, they’re the ones who started us all down this road.

Richard Ratay is the author of the upcoming book “Don’t Make Me Pull This Thing Over! An Informal History of the Family Road Trip.” Follow him on Facebook.

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  • THX1136 THX1136 on May 28, 2016

    A delightful story! (and what poor luck at the outset for the travelers.)

  • RHD RHD on May 29, 2016

    Left out of the story is whether or not he had to return to California to collect his 50 dollars.

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