Chicago Is Giving New Meaning to the Phrase “The Journey Begins Here”

In a fitting tribute to one of America’s most legendary roadways, Chicago has officially designated Navy Pier as the new symbolic starting point of Route 66, just in time for the Mother Road’s 100th anniversary. The moment marks both a celebration of history and a fresh chapter for a route that has defined American travel culture for generations.

The late March day began with a ceremonial unveiling of a new Route 66 sign at Navy Pier, anchoring the iconic highway’s starting line along the shores of Lake Michigan. From here, the story stretched westward all the way to Santa Monica Pier, reinforcing a symbolic “pier-to-pier” journey that captures the romance of the open road.

But this wasn’t just a ceremony, it was a full-on celebration of Americana, with surprises around every corner. Guests encountered everything from live performances by Plain White T’s to gleaming classic cars courtesy of the Volo Auto Museum including the crowd-favorite Batmobile. Vintage Route 66 memorabilia added a nostalgic touch, while llamas and alpacas from the Chicago High School for Agricultural Sciences brought a quirky, road-trip spirit to the pier.

There were also plenty of unforgettable characters: two Abraham Lincoln impersonators mingled with the crowd, one of them reimagined as a life-sized bobblehead, while Ms. Route 66 made an appearance, embodying the enduring charm of the highway itself. Overhead, multiple helicopter flyovers punctuated the celebration, adding a cinematic flair to an already lively scene.

The festivities even nodded to the road ahead. As one might say, if you’re doing Route 66 from its true start to finish, you begin your journey in Chicago. Your first roadside reward comes about an hour later in the small town of Wilmington, where the towering Gemini Giant, a 30-foot-tall, space-age fiberglass “Muffler Man” greets travelers. He looms large over the historic Launching Pad site, a nostalgic reminder of mid-century roadside culture. It was very fitting that a man almost 7 feet tall dressed as the Gemini Giant attended the celebration.

For those inspired to dive deeper into Route 66’s rich visual history, the Newberry offers a remarkable companion experience. Our James R. Powell Route 66 Postcard Collection features more than 4,000 printed and real-photo postcards spanning all eight states the highway crosses, primarily dating from the mid-1920s through the 1960s. The collection captures the essence of Route 66, its tourist attractions, motels, service stations, diners, and roadside architecture and preserves the look and feel of a bygone era. Visitors aged 14 and older with a valid photo ID can explore the collection in person Tuesday through Saturday from 10am to 3pm, making it an accessible stop for anyone eager to continue their Route 66 journey beyond the pavement.

It’s a uniquely Chicago moment—where history, music, spectacle, and nostalgia collide. And for Route 66, it’s not just about looking back on 100 years of stories. It’s about setting the stage for the next century of adventures, beginning once again at the water’s edge.

Kinsey Major is the Newberry’s Postcard Librarian.