Route 66 Road Trip Traces America’s Past From Chicago to Santa Monica

USA TODAY
USA TODAYMay 17, 2026

Why It Matters

The trip demonstrates how heritage tourism along Route 66 revitalizes local economies and safeguards a quintessential piece of American road culture for future generations.

Key Takeaways

  • Route 66 spans seven states, linking Chicago to Santa Monica.
  • Travelers cherish historic sites, reviving abandoned buildings along the route.
  • The journey blends nostalgia with modern road‑trip culture.
  • Local communities actively preserve and promote Route 66 heritage.
  • The trip covered 2,000 miles in fourteen days, highlighting diverse experiences.

Summary

The video chronicles a two‑week, 2,000‑mile road trip that follows the iconic Route 66 from Chicago to the Santa Monica Pier, highlighting the highway’s historic significance and its enduring cultural allure.

Along the way, the travelers encounter passionate locals, restored motels, and quirky landmarks such as the Midpoint Café—the official halfway stop—and a gift shop credited with reviving the route’s historic profile after an interstate bypass in 1987. They note that Route 66 is not a single, fixed path; purists debate the “true” alignment, while many drivers enjoy detours onto dirt roads and side streets that showcase regional character.

Memorable moments include counting license plates on a ceiling adorned with traveler gifts, standing at Winslow, Arizona, and reflecting on the road’s symbolism as a living museum of America’s past. The hosts emphasize that each state along the highway inspired unique artistic themes, underscoring the route’s role as a canvas for personal and communal storytelling.

The journey illustrates how heritage tourism can breathe new life into small towns, stimulate local economies, and preserve a shared sense of American identity, proving that Route 66 remains a vibrant conduit for adventure and cultural preservation.

Original Description

A two week Route 66 journey explores history, culture and people from Chicago through seven states to Santa Monica.
Read more: American road trip: Three generations, two cars, 2,000 miles on Route 66 https://www.usatoday.com/story/news/usa250/2026/05/17/route-66-anniversary-mother-road-family/89605580007/
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