The First Great American Road Trip: Horatio Nelson Jackson, Sewall Crocker, and Bud the Bulldog
- Daniel Holland
- Sep 15, 2025
- 5 min read
Picture it: San Francisco, 1903. Automobiles were still “devil wagons” in the eyes of many, noisy, dusty contraptions that frightened horses and infuriated pedestrians. Vermont had even passed a law requiring a man with a red flag to walk in front of every car. Outside of major cities, spotting one of these machines was almost like seeing a UFO today.
Into this world walked Dr. Horatio Nelson Jackson, a wealthy, 31-year-old physician who had recently “succumbed completely to a primary enthusiasm for the newfangled horseless buggy.” At the University Club in San Francisco, during a lively evening of drinks and debate, someone insisted a car could never cross the United States. Jackson disagreed. A $50 bet (about $1,750 today) was made, and America’s first road trip was born.
A Doctor With No Car, No Map, and No Experience
Jackson, already nicknamed “The Mad Doctor”, had little driving experience, no maps, and not even a car. What he did have was optimism, and money from his wife Bertha’s wealthy family. Within days, he purchased a 20-horsepower, two-cylinder Winton touring car, nicknamed it the Vermont, and roped in a 22-year-old bicycle mechanic turned chauffeur, Sewall K. Crocker, to come along as driver, repairman, and general problem solver.
The pair stuffed the Vermont with gear: spare parts, coats, blankets, a block and tackle, canteens, firearms, tools, and a Kodak camera. Jackson even strapped a single spare tire to the side of the car, blissfully unaware it would be shredded almost immediately.
On May 23, 1903, they rolled out of the Palace Hotel in San Francisco, made it a few blocks to the ferry terminal, and crossed to Oakland. The first breakdown came 15 miles later, when a tire blew.
“Discovering their loss, Jackson and Crocker determined that living off the countryside or starving was less to be feared than a return trip,” wrote Jackson’s friend Ralph Nading Hill in The Mad Doctor’s Drive.
This set the tone for the journey ahead.
Roads That Were Barely Roads
In 1903, America had very few paved roads, and most people rarely travelled more than 12 miles from home. Outside of cities, “roads” were really wagon trails — “a compound of ruts, bumps, and thank-you-marms,” as Jackson later put it.
It cost him dearly. By the time the journey was done, he had spent around $8,000 (the equivalent of over $250,000 today), scattered a trail of broken parts and discarded tools across the continent, and lost more pairs of eyeglasses than he cared to admit.
Along the way, they endured endless flat tires, fuel shortages, and mechanical failures. Crocker became a master of improvisation, once convincing a farmer to part with the wheel bearings from his mowing machine so the Vermont could roll on.
At one point, they had to use their block and tackle seventeen times in a single day to drag the car out of Nebraska mudholes. Jackson later remembered that day:
“We worked from 5 o’clock in the morning till dark, and then we made but sixteen miles.”
It was exhausting, expensive, and often demoralising — but also unlike anything America had seen before.
Enter Bud, the Bulldog
By the time they reached Caldwell, Idaho, Jackson decided what the trip really needed was a dog. For $15, he bought a bulldog named Bud. The alkali dust burned the dog’s eyes so badly that Jackson fitted him with his own pair of goggles, creating one of the most iconic images of the early automobile age: Bud the Bulldog riding shotgun in style.
“Bud was the only one of the trio who used no profanity on the entire trip,” Jackson quipped.
Newspapers went wild for Bud. From then on, he was as famous as the car itself, sometimes called “the chauffeur.” Children closed their schools just to see him roll into town.
A Traveling Circus
Everywhere they went, the Vermont drew crowds. Many rural Americans had never seen an automobile before. Some thought it looked like a runaway train car. Others threw up steel cables across roads to stop the “devil wagons.”
Jackson recalled:
“We would simply telephone ahead that we were coming, and the principals would close up the district schools in the villages so as to allow the children and others to see us go by.”
But their celebrity didn’t save them from mishaps. Jackson lost his coat, along with most of his cash, and had to wire his wife to send money. They endured a 36-hour stretch without food in Wyoming before a sheepherder fed them roast lamb and corn.
They also battled through what Jackson called the “buffalo wallows” of Nebraska: stretches of land so battered by rain that they swallowed car wheels whole.
Against the Odds, They Made It
On July 26, 1903, after 63 days, 12 hours, and 30 minutes, Horatio Nelson Jackson, Sewall Crocker, and Bud the Bulldog rolled into New York City. They had covered around 4,200 miles, burned through 800 gallons of gasoline, and won the bet that many thought was madness.
Amusingly, Jackson never collected the $50. The money didn’t matter. He had proven that cars weren’t just toys for the rich. They could cross a continent.
The final leg back to Vermont was classic Jackson. His car broke down 15 miles from home. His brothers came to help, and their cars broke down too. In the end, Jackson towed both of them home, only for the Vermont’s drive chain to snap at the threshold of his garage.
Why It Mattered
At the time, America’s frontier was considered closed. The railroads had knitted the nation together, but cars were still novelties. Jackson’s journey helped shift public perception. Roger White, curator at the Smithsonian’s America on the Move exhibition, later called it:
“A pivotal moment in American automotive history. The Jackson-Crocker trip excited people across the nation. It got people thinking about long-distance highways.”
In fact, Jackson’s mad gamble paved the way (literally) for the Good Roads Movement, the eventual building of the interstate highway system, and the car culture that defined the 20th century. Motels, fast-food chains, road trips — all trace a line back to that wager in San Francisco.
A Journey Remembered
One hundred years later, in 2003, orthodontist and antique car museum owner Peter Kesling set out in his own 1903 Winton to recreate the journey. He admitted:
“In the last three months I’ve been driving it every day in preparation for the trip and every day something breaks. That’s why I’m optimistic. Everything that can break has broken already.”
Filmmaker Ken Burns was there to document it, along with author Dayton Duncan, who summed up Jackson’s legacy:
“Horatio was the big guy on the road with a brand new car. He was frightening horses. Peter’s car is 100 years old, and he has to worry about semi-trucks.”
That’s the contrast: in 1903, Jackson was proving that cars could move at all. Today, the roads he dreamed of are so crowded we can hardly imagine a world without them.
Final Thoughts
Horatio Nelson Jackson didn’t set out to change history. He just wanted to win a bet, have an adventure, and maybe prove a point. But in the process, with Crocker at the wheel and Bud riding proudly in goggles, he helped launch America into the age of the automobile.
He later summed it up simply:
“Fun we have had and plenty of it, and we’re looked upon as a traveling circus.”
Over a century later, his circus still inspires anyone who’s ever felt the urge to pack up, hit the open road, and see just how far a little mad optimism can take you.
Sources
Horatio Nelson Jackson, Personal Accounts of the 1903 Journey
Ralph Nading Hill, The Mad Doctor’s Drive
Peter Cohan, Horatio’s Drive: America’s First Road Trip (PBS Documentary, 2003)
Smithsonian National Museum of American History, “Horatio Nelson Jackson’s 1903 Cross-Country Trip”
Dayton Duncan & Ken Burns, Horatio’s Drive: America’s First Road Trip (companion book, 2003)
San Francisco Chronicle archives, 1903 & 2003 retrospective coverage
https://americanhistory.si.edu/collections/search/object/nmah_1303437
