What was the first cross-country U.S. road trip?

A 1903 Winton on display at a send-off ceremony for a group of motorists who, in 2003, recreated the first car trip across the U.S. See more pictures of classic cars.
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It's hard to imagine how anyone ever laughed off the automobile as a passing fad. But at the beginning of the 20th century, many people did. According to the George Gershwin lyrics, "Ford and his Lizzie kept the laughers busy." Gershwin was referring to Henry Ford and his Model-T car, which was introduced in 1908 and nicknamed the "Tin Lizzie." Few people at the time suspected the automobile could overtake the horse as the most practical method of travel.

However, it gets easier to understand people's skepticism (and mocking amusement), when you see just how primitive and unreliable these early automobiles were. In the 1890s, one was lucky to drive a few miles without some sort of breakdown. Motorists needed to double as mechanics to constantly maintain the engines. It's no wonder that a group of gentlemen, while gathered at San Francisco's University Club on May 19, 1903, were arguing that the automobile would fade away because it wasn't useful for long distances.

As it happened, a 31-year-old Vermont physician by the name of Horatio Nelson Jackson was passing through San Francisco, and he was there that night participating in the conversation. He disagreed with the other men, arguing that the automobile had a great future. And what's more, he maintained that he could successfully drive one across the country -- a feat that few had attempted and none had yet accomplished. He even bet $50 that he could do it in less than 90 days.

After securing his wife's blessing and funds, Jackson quickly purchased a red 1903 Winton touring car that he nicknamed "The Vermont." The car had a 2-cylinder, 20-horsepower engine and no amenities to speak of -- not even a top or a windshield. He also recruited Sewall K. Crocker, a 22-year-old mechanic, to join him on his journey. He loaded up equipment, including guns, cooking gear, a Kodak camera, jacks, and a spade and fireman's axe, as well as a block and tackle with 150 feet (45.7 meters) of rope.

After just four days of planning, Jackson started his journey. Little did he know, however, that the Packard Motor Car Company was already months into planning its own automobile voyage across the country. Compared to Packard's meticulous planning, Jackson was flying by the seat of his pants. But what he lacked in wisdom, he made up for in sheer determination.

Thanks to the many letters Jackson wrote to his wife, we have a detailed account of his journey.