Jackson convinced a young mechanic and chauffeur, Sewall Crocker, to serve as his travel companion, mechanic, and backup driver. Crocker suggested that Doctor Jackson buy a Winton Motor Carriage Company car. He bought a slighly used Winton, which he named "Vermont", after his home state, bid his wife goodbye (she took the train to Vermont to meet him when he arrived), and left San Francisco on May 23, carrying coats, suits, canvas protective suits, sleeping bags, blankets, canteens, a water bag, an axe, a shovel, a telescope, tools, spare parts, a block and tackle and cans for extra gasoline and oil, a camera, a rifle, ashotgun and pistols.
Heeding the failed attempt by automobile pioneer Alexander Winton (founder of the Winton Motor Carriage Company) to cross the Southwestern desert, Jackson decided to take a more northerly route. A route through the Sacramento Valley and along the Oregon Trail also allowed them to avoid the higher passes in the Rocky Mountains.
The car was transported by ferry from San Francisco to Oakland and points eastward. But only fifteen miles into the journey, the car blew a tire. Jackson and Crocker replaced it with the only spare they had, in fact, the only right-sized spare tire they could find in all of San Francisco.
The second night of their journey, they replaced the side lanterns, having discovered on the first night that they were too dim. They stopped early in Sacramento to accomplish this. The duo was assisted in Sacramento by bicyclists who offered them road maps. Jackson was unable to buy a new tire, but purchased some used inner tubes.
Going northwards out of Sacramento, the noise of the car covered the fact that the duo's cooking gear was falling off. They were also given a 108-mile wrong turn when the directions they were given by a woman proved to be a lie so that she could send them to the spot where her family could see an automobile.
The rough trek towards Oregon required them to haul the car across deep streams with the block and tackle. Somewhere along this route, Jackson lost his glasses. And they were forced to pay $4 by an enterprising entrepreneur who required the toll before allowing them to cross his property. When their tires blew out they were required to wind rope around the wheels. Jackson did manage to find a telegraph office and wired back to San Francisco for replacement tires to be transported to them along the journey.
Reaching Alturas, California, Jackson and Crocker stopped to wait for the tires. They offered locals rides in the car in exchange for a "wild west show". When the tires failed to materialize, however, they continued on after a three-day wait.
On June 6, the car broke down, and they had to be towed to a nearby ranch by a cowboy. Crocker made repairs, but a fuel leak caused them to lose all of their available gasoline, and Jackson rented a bicycle to travel 25 miles to Burns, Oregon for fuel. After suffering a flat tire on the bicycle, he returned with fuel, and they returned to Burns to fill up.
On June 9, outside of Vale, Oregon, the "Vermont" ran out of oil. Jackson walked back to the last town to get oil, only to discover eventually that they had been stopped only a short distance outside of Vale. The next day they arrived in Ontario, Oregon, where supplies waited for them.
Somewhere near Caldwell, Idaho, Jackson and Crocker obtained a bulldog named Bud. How they got Bud is unclear -- theories of purchase, gift and theft have all been offered. It turned out that the dusty alkali flats the travelers would encounter would bother Bud's eyes so much, that Jackson eventually put goggles over the dog's eyes. (The Winton had neither a roof nor windshield.) At one point, Bud drank bad water and became ill, but survived.
At this point, the trio became celebrities. The press came out at every stop to take their picture and conduct interviews. At Mountain Home, Idaho, citizens warned them that the Oregon Trail was not good further east, so Jackson and Crocker veered off their original course along the southern edge of the Sawtooth Mountains. At Hailey, Idaho, Crocker wired the Winton Company for more parts.
On June 16, somewhere in Idaho, Jackson's coat, containing most of the travelers' money, fell off and was not missed. At their next stop, Jackson had to wire his wife to send them money to Cheyenne, Wyoming. Before reaching Cheyenne, however, the car's wheel bearings gave out, and Crocker had to talk a farmer into letting them have the wheel bearings of his mowing machine.
The travelers eventually reached Omaha, Nebraska on July 12. From there on, they were able to use a few paved roads, and their trip was much easier. They arrived in New York City on July 26, 1903, almost two months after they left San Francisco.
Horatio Nelson Jackson eventually settled in Burlington, Vermont with his wife Bertha and Bud the bulldog. In Burlington he met President Theodore Roosevelt. When World War I broke out, Jackson was considered too old, but he contacted Roosevelt, and was commissioned an officer. Following the war, he became one of the founders of the American Legion, and twice ran for Governor of Vermont. He owned the Burlington Daily News and radio station WCAX.