In 1903, Horatio Nelson Jackson, a physician from Vermont, his mechanic, Sewall Crocker, and Jackson’s dog, Bud, made the first cross-country road trip. It took the group about 63 days to drive from coast to coast.
Mudslides, torrential rain, breakdowns, and a complete lack of roads and bridges at several critical junctures impeded their travels. The adventure was an exciting and expensive one (it reportedly cost Jackson $8,000), and it absolutely captured the imaginations of Americans. In the years that followed, hundreds of other folks would set out on their own long-haul car journeys.
More than a century later, road trips remain a popular mode of vacation travel for Americans. In the summer of 2023, approximately 79% of Americans reported they’d be hitting the pavement for a leisure trip. These road trips have obviously changed significantly since those early days—for one thing, the national highway system makes long-distance travel much easier and faster—but some things, like our affinity for greasy fast food and love of a gorgeous view, have remained the same.
CheapInsurance.com explored the history of American road trips featuring photos from news agencies and media hubs. This collection of 25 images shows what driving in the country has been like over the last century. From dusty beginnings to infrastructure feats like Route 66, hit the road through images that show America’s unique and magical love affair with car travel.