Our First State on Historic Route 66

After almost 2 weeks of being on the road, we finally have a chance to take a breath, and I have a chance to update y’all on our journey! After a rough departure from Michigan, which you can read about in the last post, we headed out to Joliet, Illinois, with our trailer hooked up and hearts full of classic-road-trip excitement. Over the next few days, we traced the historic highway southwest through the heart of Illinois, trading cities and suburbs for rolling farmland, neon-signed diners, and tiny towns frozen in time. By the time we reached St. Louis, we’d logged hundreds of miles on the Mother Road, survived a dramatic Midwest storm, and fallen completely in love with this stretch of America.

Illinois is the perfect “starter course" for any Route 66 trip. The road here is well-marked, for the most part, the scenery shifts from suburban to pure Midwest prairie, and every few miles there’s another quirky landmark begging for a photo stop. We kept our pace relaxed, stopping whenever something caught our eye, chatting with locals, and always hunting for the next local delicacy or vintage gas station.

Hitting the Highway: Joliet to Atlanta

We officially started our Route 66 clock in Joliet and immediately felt the magic. Joliet’s Rock and Roll Museum of Illinois was our first stop. The welcoming energy of the locals who work and breath route 66 really made us excited for the rest of our trip. Here we got our Route 66 Passports and toured this free museum that showcased the musical influences Joliet, IL had on America and really the world.

After Joliet, the two-lane road unwound through Wilmington’s Launching Pad (that giant Gemini Giant is impossible to miss), past the old gas stations in Dwight and Odell, and on toward Pontiac with its colorful murals and vintage fire truck (and Wally’s). Every town felt like a living museum. Traveling in April we did come across a lot of businesses not open for the season yet. Don’t be discouraged to get some pictures anyway and enjoy the step back in time these vintage gas stations and garages provide.

Just before sunset, we pulled into Atlanta, Illinois, for our first overnight. We got to stay on an old alignment of Route 66 through a service called Harvest Host. We used Harvest Host for most of our overnight bookings, and so far, we have had nothing short of amazing experiences with most of our hosts!

From Atlanta to Litchfield – Classic Stops and Open Road

The next day we continued south through Lincoln, with its giant Lincoln statue and courthouse, and Springfield, birthplace of Abraham Lincoln and home to more Route 66 history than you can squeeze into one morning. We grabbed coffee, stretched our legs, and soaked up the small-town charm before pushing on. Don’t forget to check out The Mill in Lincoln. The Mill was originally an iconic restaurant on Route 66. It closed as a restaurant in 1996 and was almost demolished and forgotten. Until the Route 66 Association of Lincoln and many others worked endlessly to restore the building to its original design and structure. The entire museum has original items on display in an original building. It was beautiful to see the passion the locals had for this place. The actual windmill is being repaired and scheduled to be back up in time for their Route 66 celebrations! Their passion ultimately allowed this historical landmark to survive and thrive. Don’t miss this stop on 66!

By evening we reached our second overnight stop in Litchfield. We got to stay at the legendary Skyview Drive In Theater! It was honestly one of the coolest experiences I have ever had, besides the birds protecting their nest in the morning, and the not-so-friendly employee in the cafe/store. I have worked with dogs and animals for years, and have had my own dog for over 3 years now. When there is an animal in a business where they are not allowed, there is a polite way and wrong way to handle it. Unfortunately this one employee left a poor mark on me because of the way he handled the situation. Other than the interaction about Margarita while checking in, it was a pleasant and unique experience, and would do it again.

Litchfield felt like the perfect midpoint between the northern prairie towns and the bigger city energy waiting in St. Louis. We spent the evening watching movies and planning the final push across the Mississippi the next morning.

Rolling out of Illinois

The last morning in Illinois was pure joy—blue skies, light traffic, and that unmistakable feeling that we were really doing this. We made sure to stop by the Pink Elephant Antique Mall in Livingston before crossing the mighty Mississippi River into Missouri. The antique mall had a candy shop and ice cream shop attached. Pretty cool place but definitely more of a tourist spot, and it felt it. It was a little crowded and you didn’t get the Route 66 feel you got from some of the other shops and museums along the way.

Illinois gave us everything we hoped for on Route 66: vintage diners, friendly locals, wide-open skies, and one unforgettable storm we’ll be talking about for years. This leg reminded us why people still chase this road after all these decades—it’s not just about the miles, it’s about the stories you collect along the way. We’ll be back soon with Part 2: Missouri and Kansas! In the meantime, if you’re planning your own Route 66 adventure, Illinois is the perfect place to start. Pack your patience, your camera, and maybe an extra tarp—just in case Mother Nature decides to join the party.

Safe travels,

xoxo

H, D, M