June 2026 marks 100 years of Route 66—a highway that, since 1926, has connected the main streets of small-town America and been a symbol of freedom and westward expansion. To mark the centennial, Esquire sent three sets of road-trippers to traverse three different stretches of the iconic road. The result is a collective photo essay and journey that one traveler describes as “an emotional archive of America,” starting in downtown Chicago and ending in Santa Monica.
As we drove, we started to realize that all these roadside attractions felt fresh to us because they came from a completely different idea of what entertainment could be. There were no screens, no apps, no log-ins—just giant objects, neon signs, and roadside oddities designed to catch your eye and pull you in. A replica of the Bluesmobile from The Blues Brothers outside a travel center near Joliet shouldn’t have been as charming as it was. But that’s the thing about Route 66: What we expected to feel outdated often felt surprisingly alive. It made us realize how hungry we were for experiences that are tangible, specific, and rooted in the real world, things you can’t swipe past or experience through a screen.
More stories about road trips
Middle of Somewhere
“One remote highway in Nevada links far-flung communities that attracted settlers for generations. Why are some still drawn there today?”
Are We There Yet?
“A family trips and stumbles across 3,000 miles of Texas.”
Will Dad and I Ever See Texas the Same Way?
“A noted Texas historian and his adult child get behind the wheel to see if they can finally view their home state the same way.”
I Tried to Toughen Up My Son. Things Didn’t Go as Planned.
“A trip to the Badlands with my 8-year old offered lessons in boyhood — and manhood.”
Highway 89 Revisited
“A 1,400-mile trip through several national parks takes a writer deep into his past.”
With Melville in Pittsfield
“The true believers were nowhere in sight on that snowy morning.”
