From the Pacific to the Great Lakes: A Route 66 Journey 100 Years in the Making

January 13, 2026

Earlier this month, America’s Automotive Trust and our partners set out on a journey that embodied everything we stand for, celebrating and preserving America's automotive heritage.

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On January 3, a group of classic automobiles departed the Santa Monica Pier, beginning a cross-country cruise along the most storied highway in America: Route 66, which is celebrating the centennial of its opening in 2026. Over the course of ten unforgettable days, the convoy traveled through ever-changing landscapes, small towns, historic landmarks, and living pieces of American culture, arriving in Chicago on January 12 to mark the completion of the Route 66 portion of the drive.


From the deserts of the Southwest to the plains of the Midwest, the journey was a rolling reminder of how deeply intertwined the automobile is with America’s history. Along the way, we experienced iconic Route 66 sights like Cadillac Ranch, crossed the historic Chain of Rocks Bridge, and stopped at beloved roadside landmarks including Pops 66 Soda Ranch—each one a chapter in the story of American mobility and travel.


The landscapes shifted dramatically as the miles passed. Sunbaked stretches of road gave way to farmland, city skylines replaced open horizons, and the weather reminded us that this was a true winter drive. Through it all, historic vehicles proved exactly why they deserve to be driven, not just displayed.


When the group pulled into Chicago, the journey concluded with a visit to Navy Pier, providing a fitting endpoint to the Route 66 experience and a moment to reflect on the significance of what had just been accomplished.


This drive would not have been possible without the incredible support of our partners. We extend our sincere thanks to The Detroit Auto Show, The Route 66 Centennial Commission, and the Hagerty Drivers Foundation for helping bring this vision to life. We are also deeply grateful to State Farm, Booking.com, Only In Your State, Ambassador Wines of Washington, and Plycar Transportation for their support and collaboration throughout the journey.


We’d also like to thank the communities, hosts, supporters, and enthusiasts we met along the way, waved from the roadside, shared stories, opened their doors, and celebrated these cars with us. Route 66 remains alive 100 years later because people continue to care about its history and meaning.


At its core, this drive exemplifies the mission of America’s Automotive Trust: to preserve and celebrate automotive history by engaging with it in real, tangible ways. These vehicles and the road they traveled are more than artifacts, they are functional, emotional connections to our past. While historical in their presence, the vehicles are meant to be driven, heard, and experienced;. As for the Mother Road, it exudes car culture, American history and the significance of community. While Route 66 concludes in Chicago, it's the road we're taking home to the Motor City, because the journey isn’t over yet.


Today, the drive continues on to Detroit, where these historic vehicles will arrive just in time for the opening of the Detroit Auto Show, carrying with them thousands of miles of history, stories, and memories from America’s Main Street. Many of the vehicles will be on display during the show! If you see us come say hi!


Route 66 may be behind us, but the road ahead is just getting started. Stay tuned for more great photos, videos, and celebrations from the journey!

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By AAT • December 9, 2025
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By AAT • November 20, 2025
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By AAT • November 13, 2025
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