Summer and road trips are synonymous, with millions of Americans taking to the road in the spirit of unbridled adventure. Jack Kerouac’s 1957 novel, On the Road, fueled a generation with the romance of the open road.
But HOW did it all start?
WHO was the first to pave the way for this American tradition, WHEN, and WHY?
A Bet, Two Men, and a Dog in Goggles
On May 19, 1903, a heated debate at the exclusive University Club in San Francisco resulted in a $50.00 wager taken by Horatio Nelson Jackson. Horses and carriages were the main mode of transportation, and many thought the horseless carriage was a passing fancy of the well-to-do. Certainly not reliable enough to withstand a dangerous cross-country journey. Jackson had a grander vision and recruited Sewall Crocker to prove the automobile nay-sayers wrong.
On May 23, 1903 they set out to complete the trip from San Francisco to New York City in less than 90 days. [Horatio Nelson Jackson in the Vermont]
They packed a second-hand 20 horsepower, cherry red, Winton touring car (dubbed the Vermont) with sleeping bags, cooking gear, and supplies, then started on their daring journey. Crocker was a former bicycle racer and gasoline engine mechanic, skills they would need in the days ahead. At the time there were fewer than 150 miles of paved roads nationwide, no road signs, or gas stations. With the rigorous terrain, automobiles often breakdown. The Vermont was no different.
The Winton crossed streams and traversed winding mountain roads better suited for 
mules than man. They suffered mechanical failures early and often, and had to rely on stagecoaches to ferry new parts and blacksmiths to make repairs. In short, their trip was one obstacle after another, devoid of the amenities we take for granted on cross-country journeys today.
With mechanical fiasco after fiasco, it took 19 days to reach Idaho. There they met a bull-terrier named Bud, fitted him with motoring goggles to protect his eyes from dust, and hoped the new addition to their party would bring them luck. Bud wore his goggles, navigating from the front seat for the rest of the journey, but luck wasn’t quick to follow. [Bud sporting his motoring goggles]
Throughout bad directions that sent them days out of their way, getting stuck in a swamp, then lost in the Wyoming badlands, the team maintained a spirit of optimism. Possibly, due to the tremendous receptions they received along the way. For many, it was their first encounter with an automobile.
Fanfare swelled to a crescendo as they rolled into Chicago on July 17, and then Cleveland a few days later. In spite of the hoopla the adventure ignited along the way, the epic road trip ended as humbly as it began. The Vermont, and its three passengers, quietly rolled down Fifth Avenue in Manhattan on Sunday, July 26, 1903, at 4:30 am. The 4,500-mile journey had taken 63 days, 12 hours, and 30 minutes. Jackson won the $50.00 bet, but it cost him close to $8,000.00—including the price of the Winton, and all its repairs along the way.
Jackson, Crocker, and the adorable Bud in his motoring goggles became celebrities, pictured in newspapers across the country and featured in Winton advertisements for years to come. They proved a cross-country road trip was an attainable American dream, even if (at the time) it was beyond the means of any but the wealthy.
Route 66 became a reality decades later. After World War II, the American highway infrastructure expanded to support cross-country travel and cars became affordable for the average person. The dream of free spirited independence lived on, becoming a cultural ideal and American tradition. 
