CALIFORNIA POSITIVE
By California Broker Magazine
November 11, 2026 marks the centennial of Route 66, a 2,400-mile highway connecting Chicago to Los Angeles. To commemorate 100 years of history, celebratory events are taking place in states situated along the route leading up to the anniversary. Many events have already taken place, but there are several Southern California festivities planned for the coming months that people of all ages can take part in to rediscover the legendary road’s enduring impact.
Commissioned as part of the United States’ first federal highway system, Route 66 served as a transportation route and quickly became a symbol of the American dream, especially during the Great Depression and later the Dust Bowl in the 1930s as people fled west in search of a better life. Advertised as the “shortest, best and most scenic route from Chicago to St. Louis to Los Angeles,” it has long been associated with the great “American road trip” and the rise in car culture, known for its “kitschy” attractions, neon signs, and mom-and-pop motels situated along the route.
The famous road has appeared in numerous films like “Thelma & Louise,” “Rain Man,” and Disney Pixar’s “Cars,” along with popular songs like “(Get Your Kicks on) Route 66” by The Nat King Cole Trio, “Life is a Highway” by Rascal Flatts, and “Take it Easy” by the Eagles. It has also earned several nicknames, including “The Mother Road”—a phrase coined by author John Steinbeck from his 1939 novel “The Grapes of Wrath” to represent a road of hope for those migrating to California from the Midwest and southern Great Plains due to the Dust Bowl’s severe dust storms and drought. Another nickname it earned was “Main Street of America,” highlighting its role as a major national thoroughfare.
Here are some of the exciting events taking place across Southern California.
The best way to celebrate the centennial is by taking a nostalgic road trip on the route, stopping at iconic locations along the way.
Now through May – “Route 66” exhibition, The Hilbert Museum of California Art, Orange, CA
Artist Joan Gladstone presents a new painting series inspired by her travels, archival images, and imaginative reinterpretations of America’s most iconic highway. To honor its past and future, a portion of her artwork sales, including notecards.
March 7 – “Cruisin’ Car Show,” Amboy, CA
– Kicking off on March 7 is the second annual Route 66 Cruisin’ Car Show, taking place at Roy’s Motel & Café in Amboy, California. The all-day gathering will feature classic cars, food vendors, live music, raffles, awards, and the Ms. Amboy pin-up contest.
April 30 – “The Great Route 66 Centennial Convergence,” Santa Monica, CA
– To commemorate the date Route 66 was signed into existence—April 30—the city of Santa Monica will hold an event at the Santa Monica Pier to build up excitement for the upcoming centennial.
May 2 – “Route 66 Big Birthday Bash,” Newberry Springs, CA
– Taking place in the heart of Newberry Springs, which is situated along Route 66, this family-friendly celebration will feature food and retail vendors, classic cars and motorcycles, live music, a beer garden, horseback rides, games for kids, costume contests, and more.
June 20-21 – “The Pasadena Chalk Festival,” Pasadena, CA
– Celebrated annually, the Pasadena Chalk Festival welcomes hundreds of artists who create large-scale chalk murals on the streets of Pasadena along Colorado Boulevard, which is on Route 66. The festival is free and offers an onsite beer garden, live music, and a silent auction.
Sept. 12 – “Route 66 Car Show & Block Party,” Victorville, CA
– This free, family-friendly festival honors the legacy of Route 66 and Victorville’s connection to the “Mother Road” with a classic car show, live music, retail and food vendors, historical art displays, and more.
Sept. 18-19 – “Cruisin’ Reunion,” Ontario, CA
– On September 18-19, Ontario will host its annual “Cruisin’ Reunion” event, a free, family-friendly festival with over 1,000 classic cars, like Model Ts, Woodies, and hot rods. There will be retail and food vendors, evening concerts, and a 75-foot Ferris Wheel.
October 23-24 and November 7 – “ROUTE 66: THE MAIN STREET OF AMERICA”
– A new feature documentary “ROUTE 66: THE MAIN STREET OF AMERICA” that celebrates the remarkable stories of the legendary highway will be screened in key cities along Route 66, with historic theatres and iconic drive-ins acting as venues for the screening tour, appearances by cast and crew, and special guests. Three locations in California will screen the film, including San Bernardino’s California Theater on Oct. 23, Amboy’s Roy’s Motel on Oct. 24, and a final screening on Nov. 7 at the historic Los Angeles Theatre in downtown LA—the original terminus of Route 66.
Other Ways to Celebrate
For history lovers and those unable to attend events in person, there is also a “National Route 66 Centennial Speaker Series” where participants can learn about diverse topics tied to the infamous road, such as the history of foodways along the road, native perspectives, and more. Taking place on March 10 is a talk led by historian and author Cheryl Eichar Jett, who will draw from her upcoming book “Aprons Away: Women’s Work on Route 66” about the women who helped shape the road.
The city of Santa Monica is also holding a Route 66 song contest—an exciting opportunity for musicians to showcase their talent and creativity, with a prize of $10,000. Celebrating Santa Monica’s iconic connection to the legendary Route 66, the contest invites artists from all genres to craft an original song that captures the spirit, history, and cultural significance of the highway.
The best way to celebrate the centennial is by taking a nostalgic road trip on the route, stopping at iconic locations along the way, like the Santa Monica Pier, which is the symbolic ending point of the route. Other famous sculptural landmarks along the route include the Gateway Arch in St. Louis, Slug Bug Ranch in Amarillo, Texas, the Gemini Giant statue in Illinois, and the Blue Whale of Catoosa. Natural landmarks along Route 66 include Grand Canyon National Park, Horseshoe Bend, Joshua Tree National Park, and the Petrified Forest National Park. Along your journey, take delight in spotting remnants of the past, like mid-century architecture, neon signs, murals, retro billboards, and more.