Taking the long road: As Route 66 turns 100, fans look ahead instead of in the rearview mirror

Route 66 sign in front of the Art Institute of Chicago
The start of Route 66, which has since moved, is marked at the intersection of Michigan Avenue and East Adams Street in Chicago's Loop neighborhood in mid-February. (Phoebe Bock/MEDILL)

By Phoebe Bock

Medill Reports

In 1963, Bill Thomas took his first road trip on Route 66 from Illinois to California to visit Disneyland. Although the historic cross-country drive meant little to him as an 8-year-old, he is now helping lead this year’s centennial celebrations along what remains of the original 2,448-mile highway.

“It’s all of America, along one road,” Thomas said. “And that’s why we need to preserve it, continue to learn about it and support it, because it is our road, everybody’s road.”

Thomas is promoting the remaining 85% of the “Mother Road” as a connector of communities and a source of economic growth as a member of the Route 66 Centennial Commission, established by Congress in 2020.

As the economic development director for Logan County, Thomas has seen firsthand how tourism along the famous road helps his hometown of Atlanta, Ill., which he said has increased sales tax revenue by 43% since 2009. Last year, more than 8,000 tourists signed the guestbook at the American Giants Museum, one of the town’s roadside attractions. Co-founded by Thomas in 2022, the museum features 18- to 25-foot-tall Muffler Men statues built between 1963 and 1972.

Route 66 opened to vehicles Nov. 11, 1926, taking drivers from Lake Michigan in Illinois to the Pacific Ocean in California. One of the first roads completed as part of the National Highway System, Route 66 passed through rural towns and cities as the primary motorway connecting the Midwest to the West Coast. During World War II, it transported soldiers and materials west to the conflict in the Pacific but afterward became popular with travelers and tourists, said John Wille, curator of the Illinois Route 66 Hall of Fame and Museum in Pontiac.

Although Route 66 was decommissioned in 1985 and replaced by new interstates, the communities it touched are still around. States intersected by the road established associations to maintain its legacy, and now, businesses and towns along the “Main Street of America” are capitalizing on its history and nostalgic ties.

“It’s a good way to step back in history, step back in time,” Wille said. “You meet a lot of wonderful people along the way.”

In 2022, Gov. J.B. Pritzker announced the distribution of $4 million to local tourism bureaus along Route 66.This year, Mayor Brandon Johnson moved the official starting point of the famed road to Navy Pier, even though it historically started a few blocks away on East Adams Street outside of The Chicago Art Institute. A caravan of vintage cars kicked off the centennial celebrations in January, making the first pier-to-pier drive from California’s Santa Monica Pier to Chicago’s lakeside attraction, before continuing to the Detroit Auto Show.

Wayfinding signage tracks the path of the Historic Route 66 out of Chicago in mid-February.
Wayfinding signage tracks the path of the Historic Route 66 out of Chicago in mid-February. (Phoebe Bock/MEDILL)

Towns along the route remain surprisingly similar to the way they were 50 to 60 years ago, said Rhys Martin, president of the Oklahoma Route 66 Association. Visitors still want to experience what they remember from past trips or from older family members’ stories.

“The journey is the destination,” Martin said. “You get to intentionally slow down and connect with somebody.”

Between 2013 and 2015, Martin drove Route 66 in shorter sections and will make his first continuous drive from Santa Monica to Chicago later this year. As the “Preserve Route 66” manager at the National Trust for Historic Preservation since 2024, Martin spends time at his day job and in his multiple volunteer roles ensuring the future of roadside communities.

“This road has been evolving since the day it was created, and it’ll continue to evolve,” Martin said. “It still has a story to tell.”

Route 66 connects Americans to the past 100 years of U.S. history, Martin said. The feeling of nostalgia for a time you didn’t experience, termed “anemoia” by the Dictionary of Obscure Sorrows, is how he describes his travel. But the road also feels current, with unique stops and destinations, like the Blue Whale of Catoosa, Okla., a 20-foot-tall and 80-foot-long metal and cement statue.  

“It represents something that still has a degree of authenticity, and it’s something that’s not replicated anywhere else,” Martin said. “The value of the road today, as we’re trying to communicate it, is it’s still main street. It’s a connector of history.”  

Centennial celebrations span all eight states along the route, also bringing renewed attention to the road’s starting point in Chicago. Now beginning at Navy Pier, Route 66 continues west through the city’s neighborhoods. In 2024, Choose Chicago added wayfinding signs to guide visitors while also serving residents.  

“If you were to drive Ogden Avenue today, you might not realize that you’re on the Historic Route 66,” said Rob Fojtik, vice president of neighborhood strategy at Choose Chicago. “Route 66 is such an important part of American history, and to Chicago history. When we think about who and what our city is today, without Route 66, it would very much not be that.” 

Along Ogden Avenue, guideposts tell the history of how Route 66 shaped the development of those neighborhoods and communities, said Fojtik, who has been working to spread tourism dollars beyond the downtown Loop area.  

“Having (signs) is really great to educate both the thoughtful Route 66 traveler, but also just the average citizen,” said Fojtik, highlighting the addition of signs about electric vehicle charging stations. “If Route 66 revolutionized cross-country travel in the 20th century, electric vehicles will revolutionize long distance travel in the 21st century.” 

Chicago’s Navy Pier, pictured in mid-February, became the official starting point of Route 66 on March 25.
Chicago’s Navy Pier, pictured in mid-February, became the official starting point of Route 66 on March 25. (Phoebe Bock/MEDILL)

Although Route 66 is now known as Historic Route 66, most of the old roadway has remained an important connector for travel and source of revenue for visitors and local communities.  

“Route 66 is the story of America told through the people that live, work and travel along it,” Thomas said. “That’s its legacy.” 

Phoebe Bock is a magazine specialization graduate student at Medill.