Horatio Nelson Jackson of Vermont was many things, a doctor, a Medal Of Honor Recipient, and an early Automotive Enthusiast. Unlike many, Horatio had a feeling that the car was not just a passing fad for the wealthy, but it was going to impact just about everything in the modern world.In May of 1903 while in San Francisco's University Club as a guest, he agreed to a $50 bet (around $1,300 today) that he could drive a car across the USA. At the time he did not even own a car and had hardly any driving experience. Since he and his wife had planned to go back to Vermont in a few days anyway and he saw his wife at the train station and set out to take on the open road.Horatio began by searching for someone experienced with the handling of automobiles and found a young mechanic and chauffeur named Sewall Crocker who he hired to accompany him on the trip. Sewall suggested that they buy a Winton . Horatio found a slightly used 20hp Winton and dubbed it 'The Vermont' after his home state and final destination. Remember this was 1903, the year that Ford Motor Company was founded, the Model T was still more than 5 years away from entering production.On May 23rd the Winton pulled out loaded with all the equipment they expected they would need, as well as spare parts, and tools. Alexander Winton the founder of Winton Motor Carriage Company suggested that Horatio take a northern route as the harsh deserts stretching from California to West Texas would wreak havoc on the early 2 cylinder car. The car was ferried across from San Francisco to Oakland and the adventure was underway. Just fifteen miles into the trek a tire blew, it was replaced with the only spare tire they had with them, the only spare tire the could find in all of San Fransisco. Upon arriving in Sacramento they replaced the lanterns as the factory lamps were more suited for use in a major city with street lamps, but were almost completely useless on the open roads. The pair also was able to find some spare inner tubes but did not find any additional spare tires.Somewhere between Sacramento and Oregon the cookware fell off. A woman gave them the wrong directions on purpose so her family could see an automobile, that detour added over 108 miles to the trip. When their tires blew out, the team improvised by wrapping a rope around the wheels until they could find a telegraph office to wire back to San Francisco for replacement tires. The pair waited in Alturas, California while the tires were being sent up by train. After three days of waiting the tires hadn't arrived so they decided to push on with their makeshift rope tires. Following along the Oregon Trail the pair avoided the higher passes through the Rocky Mountains, but the route required that they float the car across deep streams pulling it with a block and tackle.It had been twelve days to travel just 352 miles from Oakland to Alturas (including the three days they spent waiting for the tires that never arrived), today that trip would take just 6 hours by car. The Winton broke down in rural Oregon and a local cowboy towed them with his horse to a nearby ranch. While Sewall made repairs to the car, they discovered a fuel leak had drained all of their available gasoline. Horatio rented a bicycle to travel the 25 miles to Burns, Oregon to get gas. The car was repaired and the pair headed to Burns to fill up the tanks. Four days later they had made it to Ontario Oregon where supplies were waiting.