US Highway 66 was established on 11 November 1926. That makes 2026 its centennial year, and across eight states, hundreds of communities and millions of road trip fans, the celebrations have already begun.
But why does a road matter this much? And what does it have to do with classic cars?
A nation on the move
Route 66 runs from Chicago, Illinois, to Santa Monica, California, weaving through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. At 2,448 miles, it was the shortest, year-round route between the Midwest and the Pacific Coast, reducing the distance between Chicago and Los Angeles by more than 200 miles.
It allowed the movement of people out of the Dust Bowl, the mobilization of military convoys during World War II, and it fed the boom of post-war automobile tourism. John Steinbeck called it 'The Mother Road' in The Grapes of Wrath, and the name has stuck.
In the 1950s, Route 66 became a staple for vacationers headed to California and road trippers looking for adventure. Motels, diners, gas stations and roadside attractions sprang up along the entire length of the road, many of which are still there today.
More than a road
Even after it was officially decommissioned in 1985, Route 66 never disappeared. It appeared in films, TV shows, songs and novels. It inspired generations of road trippers. And it became inseparable from the idea that the journey matters as much as the destination.
That idea is also central to classic car culture, and DRIVESHARE. The cars that were being built during Route 66's heyday, the Chevrolets, Fords, Studebakers and Cadillacs of the 1940s, 50s and 60s, were the cars that drove this road and are part of the same story. They're also on our platform...
Centennial celebrations in 2026
This year, communities along the entire length of Route 66 are marking the centennial with events that feel as varied and interesting as the road itself.
Springfield, Missouri was selected as the host city for the national kickoff of the Route 66 Centennial Celebration, with a concert held on 30 April 2026, the anniversary of the telegram sent from Springfield to Washington DC requesting that a new transcontinental road be named Route 66.
Where DRIVESHARE comes in
At DRIVESHARE, we think Route 66 represents something we believe in deeply: that driving should be an experience, not just a means of getting somewhere. And this year, through our partnership with Booking.com, we're proud to have played a part in putting classic cars at the heart of one of the world's most iconic journeys.
Whether it's a self-drive adventure along a stretch of the Mother Road, or an iconic American vehicle waiting for you at your destination, we want to help people experience Route 66 the way it was meant to be driven. So if you're planning a Route 66 trip this centennial year, why not explore DRIVESHARE and find the right car for the journey?
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