I think that most of us have engaged in a wager or two…probably more in fact. For most of us gambling brings little or no gain, and instead, usually loss. That is what it would bring for Horatio Nelson Jackson, as he, to his own folly, accepted a $50.00 bar bet, back in 1903. At that time, there were roads for the cars that were coming out, but they were…well, rough, and that’s an understatement. Unpaved dirt roads are notoriously dusty, rutted, and muddy in the rain. Most people, at that time, considered the automobile a passing novelty, too unreliable to survive a trip across America, but Jackson argued that they were wrong. As often happens in these barroom discussions, someone called Jackson out on his theory. He bet Jackson that he could not drive a car from San Francisco, California to New York City, New York in 90 days. Jackson accepted the challenge.
Jackson asked Sewall Crocker to accompany him on the trip. Crocker was a 22 year old former bicycle racer and a gasoline engine mechanic. Jackson was a doctor who had given up his medical practice after a bout of tuberculosis. At this point, he was looking for adventure. Crocker suggested that the former physician purchase a used 20 horsepower Winton touring car for the treacherous journey, so Jackson did, and named it the “Vermont.” Then on May 23, 1903, the two men hopped in and headed east. They had packed sleeping bags, food, and other camping supplies. Previous cross country trips had all ended in failure, and it was likely that this one would suffer a similar fate, but this was to be the first successful cross country road trip.
Horatio Jackson had little driving experience, and no mechanical knowledge, but he had his wife’s inherited fortune, and apparently that was burning a hole in he pockets. The roads he was to be on had no road signs, there was no GPS, and more importantly, there were no gas stations…plus the fact that automobiles were prone to breakdowns. The Vermont was no different, the first pit stop was just 15 miles into the trip when they blew a tire. There would be many others. Nevertheless, Jackson would win his bar bet and the $50.00 when he rolled into New York City. The mud caked Vermont, crawled down Manhattan’s deserted Fifth Avenue at 4:30 am on Sunday, July 26. The approximately 4,500 mile journey had taken 63 days, 12 hours and 30 minutes, amazing considering all the problems. So what then was the road trip folly? Just this…Jackson had won his wager with nearly a month to spare, but it cost him $8,000 in the process. I guess he could always say he made the trip.