Horatio's Drive: America's First Road Trip (2003) on Netflix

In 1903, Americans considered automobiles practical for short trips only. Horatio Nelson Jackson believed differently. He bet a man fifty dollars that he could drive an automobile across the country. Nelson paid a man to accompany him on a trip that attempted to go from California into Oregon and the Rocky Mountain states, then across the Midwestern U.S.A. and finally to New York City. Jackson's trip made him a media sensation. While Jackson, the other man, and a dog travelled by car, they encountered numerous setbacks involving mechanical difficulties. After the Jackson car started, two other teams of drivers set out from San Francisco, each trying to be the first team to reach New York.