Imagine that you’re driving down the highway on your way from Chicago out west to California. Maybe you have the top down. Maybe you’re rapping “Going Back to Cali” into your Diet Coke. Maybe Ryan Gosling is riding shotgun and you’re making him read every “Hey Girl” meme on your Pinterest “Funnies” board. Go wherever your imagination takes you.
Now imagine that as you drive you see a big blue whale on the side of the road. Or a fifty-foot-tall spaceman holding a silver rocket. Or a row of spray-painted Cadillacs nose-down in a Texas field. No, Ryan didn’t spike your Coke. You’re not seeing things. These man-made wonders are just a few of the sites along the mother of all highways, Route 66.
Route 66 was established in 1926 and covers 2,448 miles across Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California, making it one of the most epic road trips in the world. In its heyday, the Mother Road connected the main streets of countless communities across the US, boosted local economies, and provided a means for millions of Americans to experience the freedom of the open road.
Unfortunately, as was beautifully and heartbreakingly documented in the Pixar film Cars, the “Main Street of America” was bypassed in many towns in favor of the newer, more direct Interstates. By 1985 so much of the original road had been replaced by faster, flashier freeways that Route 66 was officially removed from the US Highway System. Progress had won out and many Mom and Pop establishments were forced to close their doors. But don’t think that’s where the story ends. It wasn’t just slabs of concrete that made Route 66 what it was – it was the people. The people that harnessed their ingenuity and entrepreneurial spirit to create giant jack rabbits and barbed wire museums and opened their doors to welcome travelers just as they would old friends. Looking back, it’s probably a blessing that many of these unique, quirky places were passed by the Interstate because now they’re just far enough off the beaten path that they are able to be preserved for future generations of road trippers and freedom seekers without falling victim to progress.
Today Historic Route 66 is known for taking the seemingly average aspects of life and celebrating them. There is no subject too big or too small to be honored and commemorated. But we weren’t kidding when we said that road tripping on Route 66 is an epic undertaking. That’s why we’ve got your back. Whether you’re planning to visit just the sites in your own state or tackle the road in its entirety (which is epically fun), we’ve compiled 66 Kicks that highlight the best of the best so you won’t miss a single one.
Up first, Illinois.