Chicago Names Navy Pier as New Route 66 Starting Point, Toasts Harry Caray in Landmark Celebration

Chicago is doubling down on its place in American lore—where the crack of the bat meets the hum of the open road.

At 10:30 a.m., the city will officially unveil a new chapter in transportation history, designating Navy Pier as the starting point of the legendary Route 66. The ceremony, featuring city and state dignitaries, marks a symbolic shift for the “Mother Road” as it approaches its 100th anniversary.

Chicago staple Wayne Messmer will open the event with the national anthem, setting the tone for a celebration that blends civic pride with cultural nostalgia. The morning ceremony will close with a live performance from hometown pop-rock favorites Plain White T’s.

But the day’s emotional center arrives later.

At 5:30 p.m., just steps from the newly installed Route 66 marker, fans will gather outside Harry Caray’s Tavern for the 28th Annual Worldwide Toast to Harry Caray—a beloved Chicago ritual honoring the larger-than-life broadcaster whose voice became synonymous with summer nights and baseball dreams.

Timed to align with both the centennial of Route 66 and Opening Day of baseball season, the event fuses two enduring American traditions: the freedom of the highway and the romance of the ballpark.

The guest list leans heavily into that nostalgia-meets-spectacle energy:

• Ryan Dempster, serving as emcee with his fan-favorite Caray impression
• Ron Kittle, who famously rode his Harley the full 2,448-mile stretch of Route 66
• Tom Dore, appearing as the towering Gemini Giant—a nod to one of Route 66’s most iconic roadside attractions
• Fritz Klein, bringing Illinois history into the mix as Abraham Lincoln
• Matt Wagner, adding another layer of tribute to the legendary broadcaster

As glasses raise across Chicago—and around the world—fans will toast with Budweiser to a man who embodied the spirit of Route 66 itself: bold, unpredictable, and unmistakably American.

In a city that knows how to honor its icons, this isn’t just a ceremony. It’s a reminder that in Chicago, history doesn’t sit still—it sings, it cheers, and sometimes, it hits the road.

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