Route 66 Turns 100: Festivals, Convoys and Truck Shows

Route 66 is much more than a road. It is one of the most recognizable symbols of the United States and one of the most important highways in the history of American transportation. This year marks 100 years since its official establishment on November 11, 1926, and celebrations are already underway along the nearly 2,450-mile route connecting Chicago, Illinois, to Santa Monica, California.

Although Route 66 was officially removed from the federal highway system in 1985, the legendary “Mother Road” remains a cultural and tourism icon that attracts millions of visitors every year. For its centennial, communities across Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California are hosting festivals, historical exhibits, classic vehicle gatherings, road caravans, and special events throughout 2026.

The Highway That Helped Build America

Route 66 was originally designed as a strategic transportation corridor linking the industrial Midwest with the West Coast. At a time when automobile travel was rapidly expanding, the highway made it easier to move people, goods, and services across vast regions of the country.

Its importance grew dramatically during the 1930s, when thousands of families displaced by the Great Depression and the Dust Bowl traveled west toward California seeking jobs and new opportunities.

During World War II, the highway became a critical route for transporting troops, military equipment, and supplies. In the decades that followed, Route 66 evolved into the ultimate symbol of family road trips, automobile culture, and postwar American prosperity.

A Legacy Tied to Trucking

Long before the Interstate Highway System existed, Route 66 served as one of the nation’s primary freight corridors.

Truckers hauled food, fuel, farm equipment, construction materials, and consumer goods across the country using the highway. Entire local economies developed around the steady flow of commercial traffic.

Gas stations, repair shops, diners, motels, and roadside attractions flourished thanks to the constant movement of truck drivers and travelers.

That trucking heritage remains a major part of the Route 66 Centennial celebration. Many events throughout 2026 will feature vintage truck displays, transportation history exhibits, and gatherings dedicated to the evolution of America’s trucking industry.

Centennial Events Across Eight States

Celebrations will continue throughout the year, with the largest events scheduled around the official November centennial date.

In Chicago, the eastern starting point of Route 66, visitors can explore exhibits highlighting the highway’s history and participate in special tours designed for travelers planning to drive the entire route.

Springfield, Missouri—often considered the birthplace of Route 66—will host classic car festivals, historical displays, collector gatherings, and transportation-themed events.

Tulsa, Oklahoma, one of the cities most closely associated with the route’s origins, plans major classic vehicle caravans and community celebrations honoring Cyrus Avery, widely recognized as one of the principal architects of Route 66.

Meanwhile, Albuquerque, New Mexico, will showcase its historic neon signs, vintage motels, and iconic roadside restaurants through concerts, exhibits, and cultural programs that recreate the spirit of mid-century American travel.

Iconic Stops Along the Mother Road

Travelers exploring Route 66 during its centennial year will encounter some of the most famous landmarks in American transportation history.

In Illinois, popular stops include the Route 66 Museum in Pontiac and the iconic Gemini Giant, one of the most photographed roadside attractions on the highway.

Missouri preserves historic treasures such as the Boots Court Motel and Wagon Wheel Motel, both reminders of Route 66’s golden era.

Oklahoma remains home to attractions like the legendary Tee Pee Drive-In Theater and the historic Threatt Filling Station, a service station that played an important role during the era of racial segregation.

Texas offers one of the route’s most recognizable landmarks: Cadillac Ranch, where ten Cadillac automobiles stand partially buried in the desert landscape.

In Arizona, the former mining town of Oatman continues to attract visitors with its Old West atmosphere and the famous wild burros that roam its streets.

The journey ultimately ends at the Santa Monica Pier, where the well-known “End of the Trail” sign marks the symbolic conclusion of the cross-country adventure on the Pacific Ocean.

More Than a Highway

For a century, Route 66 has inspired songs, movies, novels, television programs, and countless road trip dreams. It has also helped define much of America’s transportation identity.

For truck drivers, Route 66 represents a time when highways were more than freight corridors. They were gathering places, stories shared over coffee, and communities built around the constant movement of people and goods.

Today, as the transportation industry advances toward new technologies, alternative fuels, automation, and increasingly sophisticated logistics systems, Route 66 remains a powerful reminder of the origins of American trucking.

One hundred years after its creation, the Mother Road continues to prove that some highways never truly disappear.

They become legends.

🎵 Route 66 Road Trip Playlist

Songs That Capture the Spirit of America’s Most Famous Highway

🚛 “(Get Your Kicks on) Route 66” — Nat King Cole (1946)

🚛 “Route 66” — Chuck Berry (1961)

🚛 “Route 66” — The Rolling Stones (1964)

🚛 “King of the Road” — Roger Miller (1965)

🚛 “Take It Easy” — Eagles (1972)

🚛 “On the Road Again” — Willie Nelson (1980)

🚛 “Life Is a Highway” — Tom Cochrane (1991)

🚛 “I’ve Been Everywhere” — Johnny Cash (1996)

🚛 “Truckin'” — Grateful Dead (1970)

🚛 “Route 66” — Depeche Mode (1987)

🚛 “East Bound and Down” — Jerry Reed (1977)

🚛 “Six Days on the Road” — Dave Dudley (1963)

🚛 “Roll On (Eighteen Wheeler)” — Alabama (1984)

🚛 “Convoy” — C.W. McCall (1975)

🚛 “Radar Love” — Golden Earring (1973)

🚛 “Born to Be Wild” — Steppenwolf (1968)

🚚 Five Must-Have Songs for Truckers Driving Route 66

1. (Get Your Kicks on) Route 66 — Nat King Cole
2. Six Days on the Road — Dave Dudley
3. Convoy — C.W. McCall
4. On the Road Again — Willie Nelson
5. East Bound and Down — Jerry Reed

Whether you’re hauling freight or chasing the ultimate American road trip, Route 66’s centennial is the perfect excuse to hit the highway and celebrate a century of transportation history.

If you’re about to start a long journey, make sure you’re properly insured before hitting the road. Click here to learn more.