As the 100th anniversary of Route 66 approaches in 2026, join Pulitzer Prize winners Jonathan Bullington and E. Jason Wambsgans as they spotlight the stops and people who live along America’s highway.

Get your kicks on America's original road trip—this 2,448-mile journey from Chicago to Santa Monica is a trip down memory lane of our nation's history. Our editors and experts handpick every product ...

Our Route 66 road trip ended at the beginning, at East Jackson Boulevard and South Michigan Avenue in Chicago, where a brown sign hanging 12 feet high on a light post tells people they’ve reached the ...

Samantha travels the Illinois stretch of Route 66, chock full of history and Americana! The Illinois stretch of Route 66 is chock full of American history and Americana! Samantha meets up with her ...

Anna Matuschek, who works in Stuttgart for the German magazine Motor Klassik, rides on Route 66 outside Oatman, Arizona. Catherine Karnow Since I discovered U.S. Route 66 as a teenage hitchhiker, I’ve ...

World-renown Route 66 starts in downtown Chicago. But you’ll want to motor west to Springfield, roughly 200 miles from the Windy City, to find the best of the Mother Road. “The big cities don’t have ...

They say driving Route 66, the iconic 2,400-mile road connecting Chicago with Santa Monica, sneaks us into a bygone America, an era of neon signs and mom-and-pop diners. This waits for us, just off ...