What better place to start a Route 66 road trip in Illinois than at a prison? Hear me out – Old Joliet Prison isn’t just any prison. It’s the prison from the opening of one of the best movies ever – The Blues Brothers with John Belushi and Dan Aykroyd. Located on a bluff overlooking the Mississippi River, it only just closed in 2002 after nearly two centuries in operation. Because of its architecture, it was saved and preserved. I had a chance to walk around with Dennis Wolff, the warden when the movie was shot, to learn more about what makes Old Joliet so unique… and see what he remembers from when Belushi and Aykroyd filmed here.

What’s a Route 66 road trip without a retro burger joint? On our trip, we stopped into the Polk-A-Dot Drive In in Braidwood. Founded over fifty years ago, it’s the ultimate example of a classic American diner and has a ton of cool memorabilia and photo ops. There we met with John Weiss, author of the only guidebook on Illinois’s Route 66. While we ate, he shared all sorts of cool stories and tidbits about this part of the highway.

No car brand matches the historic, rock n roll vibe of Route 66 like old school Pontiac cars. Well in the town of Pontiac, Illinois, you can visit the Pontiac-Oakland Auto Museum to learn all about these incredible automobiles! The museum really started back when founder and director, Tim Dye, began collecting anything and everything related to Pontiac. Fast forward to 2010, he was on his way back from a Pontiac show near Chicago and saw signs for the town. After stopping and chatting with a local art museum director, he volunteered his collection if they ever thought of starting a Pontiac Museum here and the rest is history!

While Bob Waldmire passed away in 2009, his mark on Route 66 can still be felt everywhere. Born in 1945, his family often took road trips to California via Route 66, and he fell in love with the unique culture this route fostered. He became an artist and his Route 66 illustrations are world famous. While you’re in Pontiac, you don’t want to miss stopping by his Land Yacht. Long before van life was trendy, he bought this 1966 school bus and intended to make it his home. After his passing, his mother decorated the interior with his work, and today all wanderers can come in and pay homage.

Home to the Great American Road Trip, there are only two locations of this now iconic 30,000 square foot convenience store/gas station, and one of them is in Pontiac, Illinois. Of course we had to stop in and fuel up both on gas and beef jerky!

Along with roadside drive-ins, another symbol of Route 66 are tiny, independent gas stations. While most, if not all, of them have gone out of business, many of them have been turned into landmarks or museums. One of those is Sprague Super Service in Normal, Illinois. There we met with its proprietor, Terri Ryburn, who not only has a doctorate in history but did her dissertation on Route 66. She told us all about Sprague’s unique beginnings and why it’s housed in such a beautiful, Tudor Revival building.

I know what you’re thinking – maple syrup? All the way in Illinois? Yes! Illinois is actually the furthest south and west you can be to make maple syrup (well, sirup). Funks Grove Pure Maple Sirup, in fact, predates Route 66 and goes back to 1891. Really it goes back to Isaac Funk who settled here in 1824 to raise livestock. While here his family began making maple sirup and sugar until his grandson, Arthur, opened up the first commercial farm. Funks is still in the Funk family, and I met with one of the current co-owners, Debby Funk, to sample some sirups and learn why they spell it with an “i” and not a “y.”

While most of the nostalgia along Route 66 is geared towards the 1930s – 1960s. It’s all about the 1980s in McLean, Illinois. Specifically, from 1979 – 1995, aka the golden age of arcade games. Every single building in town has some sort of arcade game and you can even stay in different accommodations with their own games. I met with John Yates, the founder of America’s Playable Arcade/Museum to see why exactly he’d turned this small town into an arcade mecca.

The way I see it – when you know you’re near a presidential library and museum, it’s your patriotic duty to stop in and visit that presidential library and museum. When it comes to Abraham Lincoln, this is doubly true! 

Located in Springfield, Illinois, the Abraham Lincoln Library and Museum is dedicated to the life of our 16th president and the one responsible for issuing the Emancipation Proclamation, freeing enslaved people across the country. While there, I met with Executive Director Christina Shutt to not only learn more about Lincoln’s presidency but how he himself changed his views on solving the question of slavery.

It would be remiss of me to talk about Route 66 and not discuss the fact that for much of its heyday, not all were welcome. For many Black Americans, traveling Route 66 often meant contending with Jim Crow laws and hostile, racist businesses. The Route History Museum was created to share these stories and how, despite it all, many Black families continued to travel along this highway, relying on Black-owned businesses and the famous Green Book. We met with the museum’s director and co-founder, Dr. Stacey Grundy, to learn more about these stories and the importance of sharing them.

You didn’t think we’d do an episode on Route 66 and only stop into one drive-in, did you? Nope! Another iconic drive-in spot you don’t want to miss in Illinois is the Cozy Dog Drive In. We sampled our cozy dogs while sitting down with Buz Waldmire, the now retired owner. It was his father who created the first cozy dog, the “original” hot dog on a stick. Don’t mistake it for a corn dog, the hot dogs here are dipped in freshly made batter rather than any of the frozen, pre-made stuff. People come from all over the world to sample these cozy dogs. During our visit alone, we met people from the Netherlands!

As you approach the end of Route 66 in Illinois, make sure you stop off at Cahokia Mounds State Historic Site. Stretching 2,200 acres near Collinsville with dozens of earthen mounds scattered throughout, this site is home to the largest pre-Columbian settlement north of Mexico. When we talked with Lori Belknap, Cahokia Mounds’ superintendent, she said it’s believed that society here reached its peak about a thousand years ago. Back then this site would have housed 10,000 – 20,000 people over 120 different mounds. No one knows for sure why they began to leave but one of the theories is climate change.

You know you’ve reached the end of Route 66 in Illinois when you reach the Old Chain of Rocks Bridge. Built in 1929, this bridge connects to St. Louis, MO to Illinois, and for decades it was a useful landmark, letting road trippers know they were crossing over to a new state. Today, it’s a pedestrian-only bridge, linking 300 miles worth of trails along the Mississippi River.