How Did Americans Drive Across the Country Before Highways?

Route 66 was created in 1926 as part of the newly minted U.S. Numbered Highway System, an effort to upgrade America’s interstate roads for the burgeoning automobile age. Before paved highways like Route 66, the idea of driving across the United States was, as the Brooklyn Eagle newspaper described it in 1910, “the last call of the wild.”  

The first cross-country drivers were more like intrepid explorers than road-tripping vacationers. In 1903, a Vermont physician named H. Nelson Jackson made a $50 bet that he and his mechanic, Sewall Crocker, could drive all the way from San Francisco to New York City. 

Without service stations or motels, the two men packed like they were going on safari: a full set of tools, 150 feet of hemp rope, camping and cooking gear, a fireman’s axe, a shotgun and pistols, auxiliary fuel tanks and a single spare tire. It took Jackson and Crocker (and their dog, Bud) 63 days to complete the first successful transcontinental drive in a red 1903 Winton, now housed at the National Museum of American History.

Despite being waylaid for weeks waiting for parts and getting mired in countless mud pits, Jackson and Sewell’s highly publicized drive inspired a generation of intrepid “automobilists” to explore the country by road. And those early cross-country drives—equal parts frustrating and exhilarating—sparked a movement to build a national highway network that eventually included Route 66.