
Route 66, hailed as “The Mother Road,” stretches over 2,400 miles from Chicago to Santa Monica and has become synonymous with adventure. The route is lined with vintage diners, quirky roadside attractions, and breathtaking landscapes that tell a story of a nation on the move. These photographs taken along Route 66 give you a nostalgic glimpse into the classic American road trip.
A 1928 Image of “Bunion Derby”

In 1928, Route 66 hosted an extraordinary event called the “Bunion Derby,” a grueling coast-to-coast footrace from Los Angeles to New York City. This race was the brainchild of Charles C. Pyle, an Illinois businessman, and was intended to promote the newly established highway. Andy Payne, a young man from Claremore, Oklahoma, emerged victorious, completing the race in 573 hours, 4 minutes, and 34 seconds.
Arriving in California

During the Great Depression and the Dust Bowl era, Route 66 became a lifeline for countless families seeking a better life in California. One of the most poignant images from this period is a photograph captured by Dorothea Lange, depicting a refugee family from Tulsa, Oklahoma, who arrived in California in June 1936. The photograph, housed in the Library of Congress, illustrates the struggles of the “Okies,” as they were often called.
A Stopping Point in Texas

Tucumcari, New Mexico, became a popular stop for travelers on Route 66 in the mid-20th century. The 1956 photograph of downtown Tucumcari captures a bustling town that was often the first major stop for those leaving West Texas. The town embraced its Route 66 heritage; today, it is home to the New Mexico Route 66 Museum. This legacy is a prominent stopping point along Route 66 which is immortalized in images.
The Start of an Epic Road Trip

Route 66’s journey begins in the heart of Chicago, where a 1965 photograph captures the Art Institute of Chicago on Michigan Avenue. It lies opposite the official sign marking the start of the historic route on East Adams Street. As the route carried travelers out of Chicago via Ogden Avenue, it passed through neighborhoods steeped in history, including Cicero, once home to the infamous gangster Al Capone.
Gateway Arch, St. Louis

The Gateway Arch in St. Louis stands as a monument to the westward expansion of the United States. A 1936 photograph of the St. Louis riverfront before the arch was built reveals a busy hub filled with steamboats, a scene that would soon change dramatically. By the mid-1930s, the riverfront had deteriorated and gave way for the construction of the Gateway Arch, which began in 1959 and was completed in 1965.