Day 1 - Chicago, Illinois to Cuba, Missouri
Route 66 is something that seems to live in the back of everyone’s heads. We’ve heard about it in songs, books, paintings, and movies throughout our lives living in America. Pop culture has ingrained the idea of this historic, iconic road and the adventures along its scenic 2,448 miles into our minds but without providing the details.
I’ve always thought it would be fun to take the trip from Chicago to Santa Monica, and the opportunity presented itself in October as a celebration of my early retirement. After some time spent in the Midwest visiting friends and family and searching for fall leaves, I made my way down to Chicago to begin the long trip down America’s past.
The "official" beginning of Route 66 is at Jackson and Michigan. For the 100th anniversary they moved it to Navy Pier to mimic the ending at the Santa Monica pier.
It was a rainy beginning to the drive as I made my way out of downtown Chicago. Since I was limited on time and had to be back in California for a wedding, I chose to skip several parts of the true Route 66, and chose specific stops along the way that stood out to be the most interesting.
Joliet Prison - Joliet, Illinois
My first major stop was the Old Joliet Prison. Built in 1858 and featured in the Blues Brothers.
Opened in 1858 and shuttered in 2002, the Illinois State Penitentiary, now known as the Old Joliet Prison Historic Site was reopened to the public in 2018. The Prison is probably best known today for its appearance in The Blues Brothers. Since then, the Prison has made a number of appearances in films and television, including the fictional “Fox River State Penitentiary” in the series “Prison Break.
I was running short on time as I had a long day ahead, so I was only able to view the prison from the outside. I met a photographer who was about to take a private tour and it made me think how nice it would be to revisit Route 66 and spend more time exploring the history in greater depth.
The Gemini Giant - Wilmington, Illinois
I drove mostly freeway to get to Joliet, but after visiting the prison I made my down Route 66 through the more rural areas of Illinois. After about 30 minutes I found my first variation of the famous “Muffler Man” figures that were popularized in the 1960’s along Route 66.
The Gemini Giant is a 30 foot tall fiberglass statue that was renovated and moved to its current position, originally standing at the Launching Pad Drive-In in Wilmington, Illinois.
This was the first location that I ran into one of the many tour buses that were driving people to different sites along Route 66. This one was full of senior citizens and they were only on a day trip along the Illinois portion of the route.
In Wilmington I found the first of countless murals I would come across on Route 66. Many have been repainted or updated to reflect the 100th anniversary of the route.
Springfield, Illinois
One of the "iconic" restaurants on Route 66 was the Cozy Dog Drive-In, specializing in corn dogs. I’m not a big fan of the food, but if you're into corn dogs this is a good place. There is apparently a debate on who invented the corn dog, and this place is one of the few making that claim, originally calling them a crusty cur.
I wasn’t sure of whether to stop or not, but about 15 minutes before the exit I saw the wiener mobile, so if there was ever a sign to stop for corn dogs, this would be it.
The corn dogs were pretty good…for corn dogs. The crowd inside was a mixture of locals out for an early lunch and travelers on the beginning of their journey along Route 66.
Miller’s Service Station in Arcola, Illinois. This restored station was originally operated as a Mobile gas station under the ownership of Grandpa Miller. This was the first of many antique service stations along Route 66.
St. Louis, Missouri
I chose to drive straight through St. Louis, but got a quick shot of the arch on my way through.
Wagon Wheel Motel - Cuba, Missouri
After around 400 miles I turned into my first stay on Route 66, the famous Wagon Wheel Motel in Cuba, Missouri. Opened in the mid-1930's, this iconic hotel is the oldest continuously operating motel on historic Route 66.
Rain was falling off and on as the sun went down, and after helping a pair of little old ladies find their cabin, I ventured out into the night to take a look at the neon lights.
Photographers come from a long way to take pictures of the neon sign. Because of the rain I was the only one out that night, and in between downpours I was able to get a couple nice shots of the hotel sign. This area is in town but still feels like there is no one around for miles aside from the occasional car that drives past.
Day 2 - Cuba, Missouri to Oklahoma City
Day two began with a drive down some small town main streets in Missouri. Every corner seemed to have a Route 66 100th celebration sign or display.
Giant Rocking Chair - Fanning, Missouri.
After a short drive from Cuba, I arrived at my first stop for the day, the Fanning 66 Outpost & Feedstore. This restored service station is a perfect example of the Americana that people travel Route 66 to see. It has souvenirs, murals, friendly staff and clean restrooms.
At the Fanning Outpost I visited the world's second largest rocking chair. For a short time was first in size, but only held the title for about seven years. To be certified, it had to rock, but eventually was welded to the ground because the owner feared for tourist's lives.
Stickers were plastered all over the legs of the chair, a theme I would see throughout Route 66. While some complain that it could be considered vandalism, others love the aesthetic and the idea of people from all over the world leaving a sign that they were there.
Gary’s Gay Parita - Paris Springs, Missouri
Gary's Gay Parita. You could spend all day at this place, being a combination restored service station and collector's museum. The name is said to come from the owners Fred and Gay Mason, using the wife's first name of Gay and Parita meaning equal, as in equal partnership.
The owner seemed like a very interesting man, but was so busy talking to other travelers that I didn’t get a chance to talk to him. Maybe next time.
The collection of antique cars, signs, bikes, and just about anything you could imagine must have taken decades, and I couldn’t help but wonder who was going to inherit this craziness when the owner passes away.
Boot’s Court - Carthage, Missouri
Boots Court is another iconic motel with a distinct design and neon wrapping around the building and covering all the signs. I only stopped for pictures but didn't have time to stay the night and see everything it up.
I love this hidden police car behind the town billboard.
The Blue Whale of Catoosa - Catoosa, Oklahoma
From Carthage I drove a combination of backroads and the main freeway to get into Oklahoma. My first stop in Oklahoma was the Blue Whale of Catoosa. This fun sculpture was built by zoologist Hugh S. Davis as an anniversary gift for his wife.
The Blue Whale is probably one of the most popular attractions on the western portion of Route 66, but still never felt overcrowded. Everyone was politely waiting for each other to take their photos and explore the inside of this happy, blue whale.
Tulsa, Oklahoma
Oklahoma City was my destination for day two, which meant I didn’t have a lot of time to stop at everything. I drove down the Route 66 portion in Tulsa and stopped for a couple giants, but moved on quickly as the clouds were getting thicker and the day was almost over.
Looking back, I think the section of Route 66 from Chicago to Oklahoma City might have been my favorite. While the landscape wasn’t the most scenic like it is out West, it had more of the small town charm, and everything has been restored to reflect how nice it was back in the day. The people were friendly, there were no large crowds, and this section just seemed to represent Route 66 in it’s best form.