WATCH: Epic Route 66 Centennial Journey, Part 1

A Route 66 diner celebrates Jake and Elwood, the Blues Brothers atop the diner, in Joliet, Illinois. By Jefferson Graham for the Photowalks series

America’s first major highway, Route 66, turns 100 in 2026, and to celebrate, explore and see what all the fuss is about, Ruth and I left the South Bay Bubble, hopped a plane to Chicago, rented a car, and drove the entire 2,448 mile way, through three time zones, eight states and a whole lot of cool stops over 21 days. From Chicago where it all begins, to the end of the road, at the Santa Monica Pier. 

It was the trip of a lifetime, full of great photo ops, fantastic people we met along the way, my kind of food (pies, cakes, malts, shakes, burgers, grilled cheese, pizza) ever changing landscapes and an eye-opening experience all around.

I invite you to see Route 66 through my lens, in the first of a six-part series, beginning with the ride out of Chicago and continuing through rural Illinois. 

Coming next: St. Louis to Galena, Kansas, Tulsa, Oklahoma to Amarillo, Tucamcari, New Mexico to Gallup, Lupton, Arizona to Williams, Needles, California to Santa Monica. 

Elvis sighting in rural Illinois on Route 66 by Jefferson Graham for the Photowalks series

 

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