LIVINGSTON — For 40 years, Felipe de la Cruz Tenorio of Majorca, Spain, dreamed of driving America’s famed Route 66.
He still recalls working at a nightclub as a young man and watching Harley-Davidson riders roll in wearing Route 66 jackets. Now retired at 65, he’s finally making the trip with the same coworker who first looked up the route with him, after a “no hay huevos” (“you don’t have the guts”) dare between the two pushed them to finally book a flight and hit the “Mother Road.”
“In Spain, everyone would ask, ‘What is that (Route 66)?’” de la Cruz said. “And we would say, ‘It’s a road that goes from the east ‘til the west.’ Every time we go to dinner, we talk about Route 66, for 40 years, because we wish we could go.”
De la Cruz and his friend are far from the only travelers beginning their Route 66 journeys to traverse the historic 2,448 miles from Chicago to Santa Monica, California. As Route 66 celebrates its 100th anniversary and America its 250th, the iconic highway is drawing renewed interest as a symbol of adventure, highway travel and classic Americana.
At the dawn of the automobile age, U.S. Route 66 helped weave America together and inspired generations of Americans to explore beyond their hometown. The Mother Road also shaped a unique brand of roadside culture, inspiring songs, a television series and a landscape filled with towering, kitschy landmarks, quirky museums and neon-lit motels.
Today, an estimated 40 million travelers experience some portion of Route 66 each year, with tourism officials expecting even larger crowds during the centennial celebration. Historic Route 66 stretched 301 miles in Illinois, and events along the way now range from a Joliet jailhouse baseball game to the Route 66 Centennial Bigfoot Festival at the Pink Elephant Antique Mall in Livingston.
Route 66 was established in 1926 and officially decommissioned in 1985, replaced in many parts of the country by the interstate highway system.
While the centennial allows older generations to reminisce about a time before Route 66’s decommissioning in 1985, it also offers younger generations a glimpse into the value of human connection along the open road.
“Route 66 is more than just a road, you know?” said Joan Sestak, member of the Federal Route 66 Centennial Commission and director of community and government relations at the University of Illinois Springfield. “It’s a shared American story about mobility, opportunity and connection. The centennial celebration gives us a chance to reflect on that and reflect on what still unites us about those shared values.”
With Route 66 originally beginning near the Art Institute of Chicago, the city recently designated Navy Pier as the highway’s official centennial starting point. The redesignation kicks off a symbolic “pier-to-pier” journey to the Santa Monica Pier as communities across Illinois prepare celebrations along the historic highway.
Driving down Illinois’ stretch of Route 66 offers a glimpse into the people and establishments that kept the road alive long before the centennial festivities began in earnest this spring.
Joliet
About 40 miles down Route 66 from Chicago sits Joliet, the official Route 66 celebration Kickoff City and home to one of Illinois’s most famous landmarks: the Old Joliet Prison historic site.
The limestone prison complex operated from 1858 to 2002 as Illinois’ longest-operating penitentiary. Today, the former prison offers historic and architectural tours, attracting visitors for both its Route 66 location and its appearance in the 1980 film “The Blues Brothers.”
The prison recently hosted Illinois’ official Route 66 centennial kickoff event, featuring a historic baseball game between the Joliet Slammers and Gateway Grizzlies. Thousands gathered May 1 to celebrate, dressed in everything from team gear and Route 66 merchandise to “The Blues Brothers” costumes and prison uniforms. Actor Bill Murray, co-owner of the Joliet Slammers, also attended the event.
“Route 66 is a nostalgic pastime,” said Darrin Thurman, tourism manager at the Springfield, Illinois Convention & Visitors Bureau, who volunteered at the event. “People from all over the world want a piece of it because it’s really an epic road trip through not just big cities, but middle America. Real America.”
Thurman added that the game at the Old Joliet Prison was a fitting way to launch Illinois’ centennial celebrations, combining America’s pastime with one of the state’s most iconic landmarks.
“We shouldn’t discount this as a really special, unique place to explore,” Thurman said.
The Big House Ballgame drew 5,500 fans and concluded with a 14-3 Grizzlies victory.
Pontiac
Another hour west on Route 66 — or about 20 listens of the classic song (“Get Your Kicks On) Route 66” — leads travelers to Pontiac, where the Route 66 Hall of Fame and Museum preserves the history of the Mother Road.
Inside, visitors can walk through Route 66 history by the decade, with cases filled with vintage signs, photographs and artifacts documenting the highway’s evolution. Among the museum’s most recognizable pieces is the orange Volkswagen microbus of Bob Waldmire, the Springfield native known for his Route 66 artwork and travels along the highway. The bus served as Waldmire’s longtime home and art studio and later inspired the character Fillmore in Pixar’s “Cars.”
“Route 66 is all about our American history, and it’s all about the Americana and the people that have made it such a special place,” said Julie Alaimo, a staff member at the museum. “They live on through our Hall of Fame Museum, as well as the people that keep their memories alive.”
Alaimo recalled a young girl recognizing her grandfather in one of the museum’s photographs, as well as meeting a woman turning 100 this year who remembered traveling Route 66 as a child decades earlier.
Part of what continues to make the highway special is its ability to connect people across generations and eras, said Liz Vincent, Pontiac’s director of community enrichment.
Even the highway’s soundtrack has endured across generations, from Nat “King” Cole’s 1946 recording of “(Get Your Kicks On) Route 66” to later covers by artists including Chuck Berry, the Rolling Stones, Tom Petty and Depeche Mode.
Springfield
Just past the halfway mark of the 300-mile Illinois stretch of Route 66, Springfield offers some of the state’s most iconic Mother Road landmarks.
Also serving as a major hub for Illinois’ centennial celebrations, Springfield is expected to host the annual Mother Road Festival and the 2026 Miles of Possibility Route 66 Conference. The Illinois State Museum is set to open a new exhibition, “Miles of Memories: Stories of Route 66,” on May 23.
One of Springfield’s most influential Route 66 stops is Cozy Dog Drive In, founded by Ed and Virginia Waldmire, the parents of Bob Waldmire. The restaurant is now owned by their grandson, Josh Waldmire.
Hard to miss with its rotating hot dog sign and bright yellow lettering, the fast-food restaurant known for popularizing the corn dog also serves as a tribute to Route 66. The Waldmire family’s appreciation for the Mother Road can be seen throughout the restaurant, from a small museum space lined with historic photographs overlooking the kitchen to a gift shop filled with Waldmire artwork, centennial merchandise, postcards, posters and limited-edition Route 66 soda bottles.
The restaurant still welcomes regular dine-in crowds, with busy lunch and dinner rushes each day.
Livingston
A giant pink elephant rising above the roadside in Livingston greets travelers entering the final 50 miles of Route 66 in the Land of Lincoln, where the Pink Elephant Antique Mall has become one of the highway’s most pleasantly garish photo stops.
The 30,000-square-foot attraction, renovated from the former Livingston High School after it closed in 2005 due to consolidation, features oversized fiberglass statues, antique vendor stalls in the former gymnasium, an old-style diner and a homemade fudge and candy shop. In the fall, parts of the former storage areas are transformed into a haunted house that has ranked among the top 10 in the state.
Owners Wayne and Tonia Pickerill said the attraction draws tourists from around the world, showing maps lining the diner walls marked by pins from international visitors showing their hometowns across the globe. The business allows visitors to boondock overnight in its parking lot for free in exchange for supporting the attraction as customers, while a social media strategy managed by Wayne Pickerill’s sisters has helped expand its reach on platforms like Facebook.
They said a Pink Elephant float inspired by their mall appeared in California’s 2024 Rose Parade.
Tonia Pickerill said her favorite part about running the attraction is hearing the accents of international tourists.
“We got a boring accent here,” Tonia Pickerill said. “We don’t got one. So I walk up to people and ask, ‘Where are you from?’ They’re like, ‘How do you know we’re not from here?’ I said, ‘Because you got an accent.’”
One of those travelers was de la Cruz, who stopped at the Pink Elephant on the second day of his 18-day journey from Chicago to Santa Monica after spotting the attraction from the highway.
The road that still connects us
Pontiac’s Liz Vincent said the long road trip culture surrounding Route 66 reflects a uniquely American tradition and a slower, more community-centered style of travel that feels increasingly rare today.
Even with rising gas prices, people can still experience the highway through bus tours or by driving even a small stretch of the Mother Road, she added.
“Anybody that has ever traveled the road will tell you that you can stop to take pictures and do what you want, and that’s a great trip,” Vincent said. “But ultimately, the trip is made by the people you talk to. Just getting out of your car, meeting people, hearing their stories and sharing your own brings us back to that sense of humanity — that we’re not really all that different, even if it can feel that way today.”
More information about upcoming Illinois Route 66 centennial events can be found on Route 66 Centennial Commission
Chloe Park is an undergraduate student in journalism with Northwestern University’s Medill School of Journalism, Media and Integrated Marketing Communications, and is a fellow in its Medill Illinois News Bureau working in partnership with Capitol News Illinois.
Capitol News Illinois is a nonprofit, nonpartisan news service that distributes state government coverage to hundreds of news outlets statewide. It is funded primarily by the Illinois Press Foundation and the Robert R. McCormick Foundation.
This article first appeared on Capitol News Illinois and is republished here under a Creative Commons Attribution-NoDerivatives 4.0 International License.