Route 66 - Part 1: Westbound from Illinois
Updated: Jun 30
History
With the rise of automobile ownership in America, Route 66 was established in 1926 by linking existing roads from Chicago, Illinois, to Santa Monica, California. Known as the "Main Street of America," it passed through numerous small towns, boosting the success of motels, diners, and gas stations. In the 1930s, as depicted in Steinbeck's The Grapes of Wrath, the "Mother Road" became an escape route for hundreds of thousands fleeing the Dust Bowl. The road was fully paved by 1938. In the 1940s, Route 66 played a crucial role as a national defense route, facilitating the movement of equipment. Post-war, in the 1950s, Route 66 reached its golden era as more families owned cars and sought the allure of diners, neon-lit motels, and the thrill of the journey. The Federal-Aid Highway Act of 1956 initiated the construction of the modern Interstate Highway System, which eventually diverted travelers from Route 66, leading to the closure of many businesses along its path. By 1985, it was no longer a continuous road and was officially decommissioned. In the 1980s, preservation groups emerged in all eight states the route traversed. In 1999, Congress established the Route 66 Corridor Preservation Program, managed by the National Park Service, to aid in its preservation. Disney and Pixar released the movie Cars in 2006, after conducting thorough research to accurately incorporate nearly every character and landmark from the real Route 66 into the film.
Our Plan
I never had a strong desire to see Route 66, as I thought it consisted mostly of rundown gas stations and outdated gift shops. However, in the spring of 2026, I began hearing more about its 100th anniversary, which piqued my interest. Samantha Brown's recommendation that it was a trip worth taking was the final push I needed. As the hectic end of the school year approached in mid May, I decided it was now or never. If we were going to do this, it made sense to do it during the anniversary year, and the only available time was the first two weeks after school ended. Dan couldn't take two weeks off work, so it was just Caden and me.
Dan not joining made the trip seem even less likely. I dislike driving and being in a car, as I often get bored and carsick, preferring to nap until we reach our destination. Caden is thirteen, and most kids his age aren't exactly thrilled to accompany their mom on a cross-country road trip to see some fiberglass giants. This situation, combined with the fact that I hadn't done much planning and gas prices were around $5 per gallon, didn't exactly set us up for success.
Nevertheless, I decided that it was now or never. On May 28th, we rented a car and set off westward. Armed with both paper and digital maps, we had a general plan of which town we aimed to reach each day, with key stops highlighted. I also reserved our hotel rooms the week before to ensure we had pre-arranged accommodations each night.
Day 1
Chicago
We began our journey at the original sign in Chicago, located across from the Art Institute, marking the historic beginning of the westbound route. In March 2026, Chicago relocated the symbolic starting point to Navy Pier, creating a pier-to-pier route. We attended a White Sox game, but since we live roughly 60 miles from Chicago, we skipped the typical tourist activities in the Windy City this time.
Day 2
For the first time in my life, I rented a car on my own. The Enterprise staff seemed a bit surprised when I explained the drop off point would be Los Angeles, California in about two weeks.
Joliet
We began by saying, "Oh look, take a picture of that!" and stopping the car to get out, take a photo, and then get back in. I soon understood that it was alright if we didn't manage to see and do everything.
Braidwood, Gardner, Dwight, and Odell
Our first planned stop was The Shop on Rt 66, as Caden is a big Coca Cola enthusiast. However, it was closed, signaling that this trip wasn't tightly scheduled but rather a spontaneous adventure where we'd discover things as they came.
Wilmington
The Gemini Giant is a must-visit attraction with a great gift shop. This was the first stop where I realized we were in for a fun experience. The woman in the gift shop was incredibly kind and welcoming, and she seemed genuinely excited to wish us well on our journey. It felt like we had become part of something special.
Pontiac
The Route 66 Hall of Fame and Museum is a fantastic stop. We learned that part of the magic of Route 66 are the real life characters who devoted so much of their lives to its preservation for future generations to enjoy. Bob Waldmire was an incredible artist and one of the many inspirations for the Disney Pixar movie Cars.
We had to stop at Wally's for some road trip snacks. They have everything except Red Vines! Caden is now in charge of the maps, the music, taking pictures, and managing the snacks. Driving is the easy job.
McClean
A delightful visit to Arcadia for some stretching and gaming. A few dollars in quarters provided a lot of entertainment. Caden experienced using a jukebox for the first time!
Atlanta
Another fun stop to take some selfies with giants at the American Giants Museum.
Springfield
The Cozy Dog Drive In is a well-known spot established by Ed Waldmire (Bob's brother) in 1946. Although it wasn't the best corn dog we've ever had (we've had a lot of corn dogs...), the location offered plenty of historical memorabilia to enjoy as we ate.
Livingston and Granite City
I carefully drove across a one-lane bridge to reach the stunning Chain of Rocks Bridge. The scene reminded me of the start of a Criminal Minds episode, with a few cars around but no people in sight. I'm sure we would have been fine but we walked a few hundred yards before I decided we should turn back.
We drove 310 miles over about 9 1/2 hours and stayed in St.Louis, MO. The time went fast and there was plenty to see to keep us entertained. I think we were actually going to do this!
Love this website! Helped give me a lot of ideas for my next trip.