Route 66 may be the single most iconic piece of roadway in the United States. Starting in Chicago, the mostly two-lane roadway comes to a screeching halt at the edge of the Pacific Ocean in Santa Monica, Calif., some 2,200 miles away. It weaves its way through eight states, countless small towns and, in today’s world, the imaginations of nostalgic adventure seekers.
Once one of the main east-west arteries in the country—the “Mother Road,” as it was known....