Chicago joins St. Louis, Tulsa, Amarillo, Albuquerque and Santa Monica in a massive celebration of the 100th anniversary of Route 66 in 2026 with unforgettable road trip experiences.

Posted on November 3, 2025

In 2026, Chicago will join St. Louis, Tulsa, Amarillo, Albuquerque and Santa Monica in celebrating the 100th anniversary of Route 66, one of the most iconic highways in the United States. Spanning more than 2,400 miles, this historic road trip will provide travelers with an unforgettable journey through the heart of America, capturing the essence of freedom, adventure and exploration that Route 66 has come to symbolize. From the lively streets of Chicago to the sunny beaches of Santa Monica, the centennial celebrations will combine vintage car parades, special events and historic tours, all designed to honor the road’s rich heritage. Each city along the route will play a pivotal role in celebrating this cultural event, ensuring Route 66 continues to inspire and attract roadgoers for generations to come.

The path to freedom and adventure

Route 66 is more than just a highway—it’s a symbol of the freedom, adventure, and pioneering spirit that defines America. Since its inception in 1926, it has been a journey for explorers and a piece of the American dream. For decades, it served as the main route for westbound travelers, and it remains a treasured experience for road travelers from around the world.

As Route 66 celebrates its 100th anniversary in 2026, the celebrations will be an opportunity to commemorate its colorful past. This year will bring together a wide range of events, festivals and car rallies to commemorate the highway’s rich history. These celebrations will honor the road’s heritage while providing an exciting opportunity for new visitors to participate in its timeless appeal.

Celebrations across the road

Throughout the anniversary year, Route 66 will host an array of events designed to highlight the route’s lasting impact on American culture. From vintage car parades and caravan parades to street festivals and live music performances, there will be no shortage of activities to enjoy. These events will take place along the way, inviting travelers to experience the charm of small towns and bustling cities alike.

One of the main attractions will be the “Route 66 Centennial Rally”, where vintage cars will travel along the historic route. Participants will get the chance to drive through the same towns and cities that gave this famous highway its charm. For car enthusiasts, these parades provide a rare opportunity to celebrate American automotive history, while also paying tribute to the generations of travelers who have traversed this historic route.

Other events will include car exhibits, historical tours and live performances, all designed to immerse visitors in the culture and history of Route 66. The centennial celebrations are set to be a gathering place for both history lovers and thrill-seekers, providing a deep dive into the history of road trips in America.

Historical monuments and stunning landscapes

While the events are exciting, the heart of Route 66 lies in the journey itself. The route is full of famous landmarks, vintage restaurants, and nostalgic motels that have long been favorites of travelers. Many of these sites offer a true glimpse into the past, evoking a sense of nostalgia for the golden age of road trips.

Famous landmarks along Route 66 include the Cadillac Ranch in Texas, the Painted Desert in Arizona, and the Route 66 Museum in Missouri. The route also passes through the Grand Canyon, one of America’s stunning natural wonders, giving travelers a chance to experience history and stunning scenery.

In addition to its popular attractions, Route 66 also has a variety of hidden gems. From quirky roadside stops selling souvenirs to small restaurants serving traditional American fare, every mile offers something unique. For those looking to experience the true essence of small-town America, a drive along Route 66 is an unforgettable journey through time and culture.

The USA brand and the global appeal of Route 66

Route 66 will play a key role in Brand USA’s new global tourism marketing campaign, “America the Beautiful.” This campaign showcases the most popular destinations across the United States, with Route 66 at the forefront, as one of the most famous and beloved highways in the world.

Brand USA’s efforts will help attract international visitors to the United States, encouraging them to explore the highway’s landmarks and experience its unique cultural heritage. With its timeless appeal and historical significance, Route 66 will attract tourists from around the world, offering them the opportunity to travel along one of America’s most famous and culturally significant routes.

A journey that lasts

As we look forward to 2026, the 100th anniversary of Route 66 is a celebration not only of the highway but also of enduring American traditions. For many, a road trip along Route 66 is more than just a vacation — it’s a trip back in time. Whether you’re driving through the busy streets of Chicago, stopping at historic restaurants, or visiting roadside sights, the experience is about embracing the freedom and adventure that this road has come to represent.

Route 66 has become an enduring symbol of the American spirit, and its centennial year is an ideal time to embark on this historic journey. Whether you’re a first-time visitor or a seasoned road tripper, the 100th anniversary of Route 66 promises to be an unforgettable experience filled with history, culture and a spirit of adventure.