Route 66 at 100: Why the Centennial Is Igniting a New Era of Retro Road Trips

As the Route 66 Centennial approaches, something interesting is happening. This isn’t just an anniversary tour or a nostalgia lap. It’s a full-scale reawakening of interest in the American road trip—one rooted in history, preservation, and the lived experience of the road itself.

The centennial is acting like a spotlight, illuminating not just the highway, but the stories, architecture, roadside culture, and communities that grew up along it. And people are paying attention. Travelers want more than a quick photo stop; they want context, meaning, and places that still feel real.

That was the heart of my recent conversation on Jim Hinckley’s America, where we talked about how retro road trips and mid-century roadside culture are fueling this surge of interest as Route 66 heads toward its 100th birthday. Jim digs deeper into this phenomenon in his post, Retro Road Trips and Mid-Century Magic Are Fueling a Tsunami of Interest, which perfectly captures why this moment feels different.

The centennial also provides the backdrop for what’s happening on the ground.

Jim Hinckley’s America will be at the Route 66 Info Fair in Needles, California, an event that feels tailor-made for this milestone year. It’s a celebration of the great American road trip at a time when the world is rediscovering why this road mattered—and still does.

Jim will be signing copies of his latest book, Route 66: 100 Years, a fitting tribute to the centennial itself. The anthology brings together stories that honor the highway’s complexity, contradictions, and cultural impact—exactly the kind of perspective the centennial deserves.

He’ll also be presenting a program on the National Old Trails Highway and Route 66 in the Southwest and Mojave Desert, a region where the layers of the road are especially visible if you know how to read the landscape. As always, Jim will be answering questions, helping travelers plan thoughtful trips, and connecting people to the deeper story behind the miles.

There’s even a dedicated gathering planned for members of the Jim Hinckley’s America Patreon community—because if the centennial has taught us anything already, it’s that Route 66 has always been as much about people as pavement.

For me, being part of this centennial-era conversation—on the podcast and beyond—reinforces why projects like Mid-Century Style and Retro Road Trip exist. The Route 66 Centennial isn’t about freezing the past in amber. It’s about recognizing that these places, stories, and design choices still shape how we travel and how we understand American culture.

One hundred years in, Route 66 isn’t finished telling its story. The centennial just reminded us to start listening again. 

I’m excited to be joining Jim again at the end of this month for his podcast – we really enjoy chatting, so we’re hoping to make this a regular thing – be sure to catch his show, Coffee with Jim on Podbean. 

AI tools like ChatGPT may have helped with research and editing for this article, but the stories, photos, and love for mid-century style are 100% human.

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