Watch Horatio's Drive: America's First Road Trip for Free: How to Stream the Movie Online at 123Movies. . In the spring of 1903, on a whim and a fifty-dollar bet, Dr. Horatio Nelson Jackson set off from San Francisco in a 20-horsepower Winton touring car hoping to become the first person to cross the United States in the new-fangled "horseless carriage." Most people doubted that the automobile had much of a future. Jackson's trip would prove them wrong.