Route 66 celebrates 100 years: The ultimate guide to driving America's most famous road trip

As the iconic Route 66 marks its centenary in 2026, travel editor Ted Thornhill of The Independent offers a guide to experiencing the "good old days" along the historic 4,000-kilometer journey from Chicago to Santa Monica. This route, which has evolved into a cultural phenomenon, is being celebrated this year, making it an opportune time to explore its legendary status.

The article delves into how Route 66 acquired its iconic standing, starting with its establishment in 1926 and completion in the late 1930s. Spanning eight states, it became a symbol of opportunity and adventure. Its cultural significance was amplified by John Steinbeck's "The Grapes of Wrath," which famously dubbed it the "Mother Road" as hundreds of thousands of Oklahomans and others migrated west during the Dust Bowl.

Following World War II, the rise of automobile ownership transformed Route 66 into a symbol of American road trip culture. Neon-lit motels and diners dotted the landscape, offering a quintessential experience of adventure and freedom. Despite its official decommissioning in 1985 and replacement by the interstate highway system, Route 66's fame only grew, spurring preservation efforts for its roadside attractions.

Today, Route 66 comprises a series of historic segments. The journey traditionally begins in Chicago, the "Windy City's" historic gateway to the west. The Independent's guide provides insights into the recommended time needed for the trip, must-see sights that make the adventure unique, and the best motels to stay in for an authentic "good old days" feel. The pilgrimage concludes at the Santa Monica Pier, where travelers often perform rituals to mark the end of this life-defining journey.