Thinking about taking a trip along Route 66 in Illinois? We sent four Mile Markers, Nathan Michael, Grant Legan, John Stoffer and Dan Kelleghan, on an epic road trip along the Mother Road over the course of three days. Discover their firsthand accounts of the experience and what stops they recommend.
Q: Out of all the stops you visited on Route 66 in Illinois, what stands out as most memorable and why?
Nathan Michael: I loved Pontiac. It’s a true American staple. The locals were so friendly and there was visually a ton of inspiration to take in.
Route 66 Hall of Fame & Museum in Pontiac by Grant Legan
Grant Legan: Definitely the two cell jail and Pontiac. But much of traveling for me is about the people you are with and the experiences you create together. Info wise, I enjoyed the Lincoln History museum in Springfield, it was a beautiful museum. The first stop for food and chicken potpie [Dell Rhea’s Chicken Basket] was my favorite as well, the owner gave us a deep history of the location and the food was incredible.
Two-cell jail in Gardner by Grant Legan
John Stoffer: The Abraham Lincoln Museum. Not for photo opps but for the history.
Dan Kelleghan: I really liked the two-cell jail because of how it reminded me of the Wild West period. It made me feel like I was living in a different time.
Q: Which attraction or location surprised you the most and why?
Nathan Michael: The Lincoln Museum. It truly gave me a deeper understanding of our country’s roots. I assumed that it would be outdated and un-emotive, but it was the complete opposite. I thoroughly enjoyed the detail and modern storytelling. I would gladly go back again.
Abraham Lincoln Presidential Library & Museum in Springfield by Dan Kelleghan
Grant Legan: Definitely the Lincoln History museum, the features and displays were so captivating. Also Pontiac was a fun little town, and Bob the Mayor was a delightful man to chat with.
John Stoffer: Springfield surprised me! I had no idea how much was happening down there.
Dan Kelleghan: I was blown away by the presentation at the Lincoln Museum. I’ve never seen anything even close to that in my entire life.
Q: Did you realize there were so many attractions in Illinois?
Nathan Michael: In Chicago? Yes. In the rest of Illinois? No. I was pleasantly proved wrong. Heading outside the traditional borders of Chicago was the best thing I’ve done all year. Really.
Grant Legan: Had no idea!
John Stoffer: I had no clue and I’ve been living in Illinois my whole life.
Dan Kelleghan: No way! Especially not that many iconic food spots.
Pie at the Palms Grill Café in Atlanta by Nathan Michael
Q: What is one word you’d use to describe your trip?
Nathan Michael: Greasy. Just embrace it. You’ll thank me later.
Grant Legan: Adventurous
John Stoffer: Full. Of stuff to do and tasty food.
Dan Kelleghan: Enlightening.
Q: What is one piece of advice you’d give to someone traveling down Route 66 in Illinois?
Nathan Michael: Enjoy the ride. Savor the time along the way and don’t hesitate to stir up conversation with the locals. Believe me; everyone has a good story to tell if you just give them enough time to share it.
Grant Legan: Stop often and ask locals for their favorite spots, we found some great bars in Pontiac that way, and some awesome antique markets that weren’t on the timeline.
John Stoffer: Take your time. Explore the back roads, the places the less travelled. Those are often the best and most beautiful.
Dan Kelleghan: Take your time and exercise often to work off all the calories from the great roadside restaurants.
Q: What meal or dish was your favorite?
Nathan Michael: I really enjoyed the Cozy Dog Drive In. The atmosphere was an overdose of true American nostalgia and they paired it perfectly with just the right food. I mean, who can turn down a dipped corn dog, fresh cut fries, and an ice cold Coke? No one.
Cozy Dog Drive-In in Springfield by Nathan Michael
Grant Legan: The first chicken pot pie. I want it right now…and for the rest of time.
John Stoffer: The classic chicken basket at Dell Rhea’s. Getting the whole history from the owner as we were eating made it that much better.
Dell Rhea’s Chicken Basket in Willowbrook by Nathan Michael
Dan Kelleghan: All of the burgers. Literally all of them.
Q: What is your favorite photo from the trip?
Nathan Michael: By far, “Death By Thunderbird.” To no one’s surprise, Route 66 has an endless amount of beautiful vintage cars. You can’t help but be inspired to take a few pictures along the way. This gem not only slayed my heart, but unfortunately severed John’s head too 😉
Captured in Springfield by Nathan Michael
Grant Legan: I had fun playing with #MiniAbe and creating funny positions for him to hang out in. He was a great addition to the trip. Him looking at the map was cracking me up in real life, and the photo is a memory of that laughter. He’s such a celebrity.
Mini Abe planning his Route 66 adventure by Grant Legan
John Stoffer: “Made it to the capitol”. Loved the night time scene with the capitol building in the background.
Illinois State Capitol Building in Springfield by John Stoffer
Dan Kelleghan: I really enjoyed using the smoke bombs that John brought… Definitely a great way to turn an OK photo into a great one!
Captured along Route 66 by Dan Kelleghan
Q: What is your go-to road trip game? Or do you have a favorite road trip song?
Nathan Michael: For me it’s probably the “Quiet Game” or “See Who Can Hold Their Bowels The Longest After a Fried Chicken Lunch.” I’m not really good at either, but I really love cranking up “One Headlight” by the Wallflowers when hitting the road.
Grant Legan: Foals: My Number. Favorite game is how much fried food can you eat in one day… But really my favorite game is when someone says let’s stop and take a photo, don’t question it JUST DO IT.
John Stoffer: The best thing for me was just sharing music that we loved with each other. Grant had made a road trip playlist that lasted us all the way down to Springfield.
Dan Kelleghan: Not really a game player myself but listening to the band Real Estate has been really great for road trips
Q: Anything else you’d want to share about experiencing Route 66 in Illinois?
Nathan Michael: There’s something special that happens when you get a broader view of your surroundings. Whether a born and raised local, city dweller, or someone having a hankering to travel; I would highly suggest taking a road trip in Illinois as soon as possible. It will give you a deeper appreciation for the people around you and it’s an affordable way get re-inspired.
Grant Legan: I really think we had a great group of guys for a trip like this. I would definitely love to share the adventure with others and tell them to stop as often as possible and explore some of the small towns a bit more. Those little cafes and bars and random shops were great to discover.
John Stoffer: Getting out of your bubble seems hard, but Route 66 is worth it and it’s in our own backyard.
Dan Kelleghan: Illinois has a lot more to offer than people realize. It’s got incredible history, food, and the friendliest people as well.
Thanks to our partners for making this trip possible, including Visit Pontiac, Illinois Route 66 Scenic Byway, Springfield Convention & Visitors Bureau, Lydia’s Loft Pontiac and The State House Inn in Springfield, An Ascent Collection Hotel.
Want to follow in our Mile Markers’ footsteps? Travel the map below!
Meet the Mile Markers:
Born in England and raised a Texas southern boy, Nathan has traveled around the United States, living in West Palm Beach, San Francisco, and finally landing in Chicago. As a photographer and designer, Nathan is driven by artistically capturing people and their stories.
Grant is a Visual Storyteller and travel enthusiast. Based between Chicago and Los Angeles, he is an experience driven creative constantly on the go.
John is a photographer based in Chicago, who owns a wedding photography business with his wife, Maura. He enjoys good music, family, coffee, bike rides and more.
Dan Kelleghan is a Chicago photographer and self-titled professional “road tripper.”