Route 66 100th Anniversary: Vintage Cars Drive Cross-Country | Santa Monica to Chicago (2026)

Get ready to hit the road and relive a piece of American history! 2026 marks a monumental milestone—the 100th anniversary of Route 66, the iconic highway that has captured the hearts of travelers for generations. But here's where it gets exciting: a group of drivers is kicking off a cross-country adventure to celebrate this 'century of adventure' in style. And this is the part most people miss—it's not just about the road; it's about the stories, the towns, and the people who keep the spirit of Route 66 alive.

On Saturday, January 3, 2026, nine meticulously restored, vintage vehicles inspired by Route 66's golden era will roar to life in Santa Monica, California, ready to retrace the legendary path. Their destination? Chicago, where they’re expected to arrive nine days later on January 12. But the journey doesn’t end there—after conquering the Mother Road, these vehicles will head to Detroit to take center stage at the Detroit Auto Show starting January 14.

Organized by the American Automotive Trust, The Drive Home VII: Route 66 isn’t just a trip—it’s an invitation. Drivers from all walks of life are encouraged to join the convoy for any part of the route, whether it’s a few miles or the entire 2,400-mile stretch. Along the way, the journey will spotlight historic stops like Barstow, California; Albuquerque, New Mexico; Amarillo, Texas; and Springfield, Illinois, among others. These aren’t just pit stops; they’re living testaments to the resilience of small towns that thrive despite being bypassed by modern highways.

But here’s where it gets controversial: While Route 66 is celebrated as a symbol of freedom and adventure, some argue that its romanticized past overshadows the economic struggles of the communities it once supported. David Madeira, CEO of the American Automotive Trust, addresses this head-on: 'This drive isn’t just about the road—it’s about honoring the motels, diners, and shops that have clung to life, even as the world moved on. It’s a reminder that the heart of Route 66 beats in these forgotten places.'

So, as we gear up for this historic celebration, we’re left with a thought-provoking question: Can Route 66’s legacy truly thrive without addressing the challenges faced by the communities it left behind? Share your thoughts in the comments—do you see this as a nostalgic journey or a call to action? Either way, one thing’s for sure: this centennial celebration is more than a drive—it’s a tribute to the enduring spirit of America’s most famous road.

Route 66 100th Anniversary: Vintage Cars Drive Cross-Country | Santa Monica to Chicago (2026)

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