Route 66 centennial caravan sets June eastbound trip from Santa Monica to Chicago

By AI, Created 4:44 PM UTC, May 18, 2026, /AGP/ – The Route 66 Main Street of America Centennial Caravan will drive east from Santa Monica to Chicago from June 6 to June 25, with organizers positioning the trip as a public celebration of the highway’s 100th year. The road trip will feature preservation groups, sponsors and roadside activations across all eight Route 66 states.

Why it matters: - Route 66 is entering its centennial year, and the caravan is meant to keep attention on the highway’s cultural and economic value as it moves into its second century. - The trip is designed to draw visitors, support communities along the route and encourage preservation of the Mother Road’s landmarks and businesses.

What happened: - The Route 66 Main Street of America Centennial Caravan announced its daily schedule for a summer road trip marking 100 years of Route 66. - The caravan will leave Santa Monica on Saturday, June 6, and arrive in Chicago on June 25. - The route will run eastbound across all eight states on Route 66. - Organizers chose the eastbound direction to increase community engagement along the way. - The event is organized by the Route 66 Road Ahead Partnership and other partners. - The US Route 66 Centennial Commission designated the caravan as an official Route 66 Centennial activity.

The details: - The caravan includes representatives from statewide Route 66 preservation and advocacy organizations. - The National Trust for Historic Preservation is part of the core group of vehicles. - The public is also invited to participate in the caravan. - Best Western Hotels & Resorts is the official hotel sponsor. - Best Western is marking its 80th anniversary alongside the caravan. - Best Western will donate more than 250 room nights along the route. - Stuckey’s will provide pecan log rolls for travelers. - Stuckey’s also plans family-friendly activations at select stops. - The Big Texan Steak Ranch of Amarillo, Texas, will bring a giant cow and trailer. - The Big Texan will host a local grilling event each evening. - Each event will invite two challengers to attempt the restaurant’s 72-ounce steak challenge. - Guests who finish the steak and all trimmings within an hour eat for free. - Media is invited to attend the grilling events. - Detailed daily stops are still being finalized and will be posted as sites and times are confirmed. - Updates and itinerary information are available at route66caravan.com. - The itinerary is being developed with support from Route 66 Navigation.

Between the lines: - The eastbound route breaks from the more familiar westward Route 66 road-trip narrative. - The sponsor mix blends preservation, travel, nostalgia and tourist attractions, which signals an effort to turn the centennial into a broad public event rather than a single ceremonial drive. - The caravan’s mix of state groups, national preservation groups and consumer brands suggests organizers want both heritage credibility and mass appeal.

What’s next: - Organizers will finalize daily stops and publish site and time details on the website. - The public can join by driving part of the route, greeting the caravan at stops or gathering along roadside attractions. - Route 66 centennial partners will continue promoting the journey ahead of the June departure.

The bottom line: - The Route 66 centennial caravan is turning a highway anniversary into a cross-country celebration aimed at preserving the road’s legacy and boosting the communities that still define it.