100 Years of Kicks: Celebrating Route 66 With Caravans, Concerts and Classic Road Trip Culture

By Jessica Parks, Staff Writer

Route 66 turns 100 in 2026. The iconic highway spanning from Chicago to Santa Monica, Calif., is celebrating its centennial with a yearlong celebration crossing the eight states that are home to the beloved U.S. highway.

Encompassing the many facets that make the roadway iconic, the centennial events are rooted in history, travel and tourism. The events provide a fun way to celebrate “America’s Mother Road” and should appeal to all types of enthusiasts. As one of the nation’s most famous transportation corridors, Route 66 also highlights historic infrastructure and community preservation.

The April 30 launch event in Springfield, Mo., commemorates the 100-year anniversary of the telegram sent from the city to the nation’s capital proposing a new transcontinental road named Route 66. A kickoff concert featuring “A-list entertainment” held at the Great Southern Bank Arena at Missouri State University will be the first of many events within the official centennial celebration. As one of the host states, Missouri has invested more than $1 million to help cities across the state hold events and design tourist attractions as part of the celebration.

Events will take place prior to the National Centennial Kickoff Celebration, with the April 30 event kicking off the anniversary’s main series.

It wouldn’t be a celebration of the 2,448-mile historic highway without a road trip, and for the 100-year bash, there will be plenty for Route 66 enthusiasts who are hitting the road.

The first “Centennial Caravan” will depart California on Jan. 2 and make the trek to Chicago, ultimately concluding at the Detroit Auto Show, scheduled for Jan. 12. The public is invited to join the party as it passes through their area.

Fast forward to June, when another caravan, coined “The Main Street of America Route 66 Centennial Caravan,” will take place to highlight historic preservation initiatives taken across the eight Route 66 states and spotlight challenges faced in the continued preservation of “America’s Mother Road.”

This caravan, organized by the Route 66 Road Ahead Partnership, serves as an homage to the 1952 cross-country cruise to honor the roadway’s nickname as the Will Rogers Highway. The partnership comprises organizations that have pledged to support the well-being and economic resilience of Route 66 communities.

The annual Great Race, a long-distance, time-speed endurance rally for vintage cars rally traversing different scenic routes across the nation, has also joined in on the festivities. This year’s event will kick off in Illinois and follow America’s Main Street to California, packed with events and special activities to take part in all along the way.

On June 27-28, in Tulsa, Okla., the Route 66 Road Fest, an event hosted by AAA, will take place. It will feature a road trip through time along The Mother Road as you experience the sights, sounds and people from the 1920s through present-day with the many interactive exhibits on display. To honor Route 66’s popularity among road trippers, the event will present an RV experience — serving as an RV park of sorts that will showcase vintage and modern RVs, immersing attendees in both class and contemporary road travel.  

The history of the automobile is interwoven with the history of America’s Main Street, which will be exhibited with a car show displaying everything from the Model T — one of the first vehicles to traverse the roadway — all the way to the present-day with the introduction of autonomous vehicles.

The two-day event will be packed with family friendly activities, including the Boy Scouts of America’s signature Pinewood Derby, miniature golf on a custom-built Route 66 course, Hot Wheels races, a virtual reality experience and much more.

Celebrate Route 66 history from the comforts of your home with the release of the documentary “The Main Street of America,” “Travels with Darley Route 66” an eight-state, eight-episode adventure across the roadway and the documentary series “The Route 66 Untold Story of Women.”

Other centennial events include orchestra performances, an art quilt project, a travel map project and much more listed on the official centennial website.

All events included in the centennial celebration are approved by the Route 66 Centennial Commission, which is organizing the multi-state, yearlong event into a cohesive package for all to enjoy.