Route 66 Adventures: Chicago to Springfield, Illinois

We started at the beginning of the Mother Road in downtown Chicago but now it’s time to hit the two-lane highway!

We are making our way down to Springfield, the capital of Illinois. Oddly enough, Illinois was the first state to hard surface their section of Route 66 and yet the first to decommission it.

Joliet, first stop on the road

The Old Joliet Prison has made appearances in many films and television shows but most notably in The Blues Brothers movie circa 1980 and the Prison Break television series.

Officially closed in 2002, there’s not much here but a fence triple wrapped in barb wire, a closed off abandoned building and a parking lot with a few old signs describing the history of the correctional facility. I was told the city used to allow visitors to roam around until this summer when the prison caught fire on two separate occasions. It would be great if they had some kind of tour, there’s a lot of history going back to 1858 when it was built.

Other Route 66 attractions in the area include Rich & Creamy ice cream store, Union Station (a new brewery is set to open this week inside), Route 66 Raceway (for racecar fans), Joliet Area Historical Museum and Route 66 Welcome Center and the Route 66 Diner.

*Tip: As far as downtown Joliet goes, I suggest not to walk around on your own on the weekends when most businesses are closed or too late at night. 

If you are hungry we recommend skipping the diner – since you will be coming across MANY on your journey – and visiting Chicken-N-Spice instead. Established in 1979, it is a favorite among locals and visitors alike. Try their big juicy chicken chunks and spicy rice.

Route 66 Illinois
Chicken-n-spice and all things nice

Another highlight of the area, is the Rialto Square Theatre, originally opened in 1926. The lavish vaudeville movie palace has been restored to all of its glory. They have shows throughout the year, history tours, and paranormal tours. It’s closed today unfortunately but maybe we will make it back for a tour some other time.

A Giant and a Delicious Pulled Pork Sandwich in Wilmington

What would Route 66 be if not for its kitschy and quirky stops? In front of the old Launch Pad Drive-In is the home of the first GIANT muffler man we see on the road. I write first because from what I’ve read there will be many more. The Gemini Giant with his silver space helmet and rocket ship is hard to miss.

When we walk up to the base to get our obligatory photo we see two young teenagers. They are laughing and posing in his legs while the dad snaps a few pictures. They rush up to me and ask if we are driving Route 66, I say yes that it is our first day. Animated and excited, the boy and girl both start talking at once. They did the trip years back when they were in grade school with their parents and loved it. Their enthusiasm is contagious, I almost skip back to the car with a big smile on my face.

My brother, who doesn’t live too far, recommended Nelly’s and we’ve been meaning to stop here for years when we pass by on I-55. What better time than now, our first official day on Route 66. ​They have about a dozen Angus beef burgers to choose from or the option to build your own. I built my own while the hubby ordered the pulled pork. As much as I enjoyed my burger, oh that pulled pork. YUM!

Going to Jail in Gardner

Route 66 Illinois
Just a random house we saw in Gardner, Illinois on Route 66
Route 66 Illinois
All decked out!

Gardner was a quick stop to the two-cell jail and historic streetcar next door. The jail was built in 1906 and is a fun photo op!

Got thrown in the slammer on Route 66 y’all!

Route 66 Illinois
Two Cell Jail in Gardner
Route 66 Illinois
Gardner, Illinois

Right next door to the jail is a historic streetcar, it was moved to Gardner in 1932 to serve as a diner along Route 66. We read that it was previously pulled by a horse and carriage!

Route 66 Illinois
Historic Streetcar Diner in Gardner, Illinois

Making Friends in Dwight

We discovered a secret about Route 66 at the Texaco Station in Dwight. There is a camaraderie among travelers and business owners that I believe we will see throughout our entire ride on the Route.

For some reason, I didn’t think about this perspective before the trip. I am realizing the journey along Route 66 might be similar to the pilgrimage we did earlier this year. Not as far as the walking goes but the idea that everyone we meet is connected by one journey. And that connection will wield kindness and kinship.

As we walked up to the Ambler-Becker Texaco Station, for instance, we were immediately greeted by a grinning woman. She asked where we were from, if we were driving the whole route and what stops we already made. She wasn’t just asking, she genuinely cared.

Here we also met a man from Michigan with a rad classic purple Studebaker toting a Route 66-themed teardrop. He has made the drive a few other times and shared some of his favorite stops along the way. He gave us a tour of his cute trailer which had Route 66 curtains, pillows, and even the knobs in his kitchen.

Click HERE to see a video of inside the trailer

Route 66 Hall of Fame in Pontiac

Pontiac is home to a few museums but we only had time to stop at one, the Route 66 Hall of Fame and Museum. It is free and has the largest collection of 66 memorabilia in Illinois. We browsed through photos and artifacts that follow the history from the beginning in 1926 to the current preservation efforts of the historic by way.

It is in the museum we are introduced to Bob Waldmire, a Route 66 aficionado and legend. He spent years documenting and sketching all things Route 66. He has been connected to the by way since birth. His father and friend invented the corndog made famous at the Cozy Dog Drive In.

Waldmire spent his whole life traveling along 66 in either a school bus turned mobile home (below), a 1964 Mustang, or a 1972 Volkswagen. You can see the real VW and school bus at the museum. Pixar and Disney based the VW Volkswagon, Fillmore, in the movie Cars on him.

The school bus has solar panels for elecricity, a rain water collection system, a cozy back patio, a storage loft, and a workimy toilet and shower. It’s pretty impressive! I couldn’t believe it was street legal; I would be shocked to see someone cruising down the road in it.


Behind the museum is a must-stop photo op!

We took a short walk around the square and found a couple more picture worthy murals.

The Land of Lincoln in Springfield

Our first overnight of the trip is in Springfield, the state capital of Illinois, also known as the land of Lincoln. The 16th President lived, worked, and was buried in Springfield. On separate trips we have visited Abraham Lincoln’s home and tomb so this time we went straight to the Presidential Library and Museum.

The exhibits follow Lincoln’s life from the very beginning to the tragic end. Kudos to them for a fabulous job bringing history to life. 

We highly recommend a visit if you are ever in the area.

Read below for information on where we stayed in Springfield

Obed and Isaac’s, a brewery on Route 66

Obed and Isaac’s is a brewery with charm. Springfield’s first microbrewery, located in a renovated historical home, is just steps from Abraham Lincoln’s home where he lived from 1844 to 1861 before becoming the 16th President of the United States.

You have the choice of inside seating in the mansion, outdoor seating on a quiet patio or a picnic table at the bocce garden. The atmosphere is top-notch for a good time.

Of course we had to try the Mother Road APA!

Engrained Brewery, a perfect stop for dinner

Engrained Brewery is fairly new on the scene, but the combination of a locally sourced restaurant and reviews of excellent beer had us intrigued.

The building and layout is a bit sterile compared to the fun ambiance at Obed and Isaac’s. But the delicious food made up for any misgivings. We had the Heirloom tomato salad, fish n chips, grilled chicken with sauteed vegetables, and raspberry shortcake for dessert.

Angela’s favorite beer: Blackberry IPA and Peach Saison

Dave’s favorite beer: German Lager and Oatmeal Stout

Route 66 Illinois
Dinner at Engrained Brewery

Our last stop in Springfield was a recommendation from one of our readers. We were told to stop by Maid-Rite Sandwich Shop for a loose-meat sandwich. The sandwich shop in Springfield was built in 1924 and claims to have the first drive-thru window in the U.S. The building, along historic U.S. Route 66, was added to the National Register of Historic Places in 1984.

I’ll be honest when I read the description of what it is- loose ground meat with pickles, onions and mustard- it didn’t sound too enticing but we were willing to give it a try!

We opted to check out the inside. The minute we walked in, I could smell the root beer. So naturally we had to order one to try.

Even when I opened up my sandwich wrapper and looked inside it still didn’t sound or look enticing but it was good and the root beer even better.

*Tip: Skip the fries and just go for a root beer and sandwich*

Springfield Illinois Lodging

We stayed at the State House Inn, a boutique hotel located near the state capitol building and Lincoln Home National Historic Site. It was perfect for what we needed. Clean room with a good location and a free hot breakfast. My only complaint is the pillows; they were big round balls. Sounds comfy right?

Route 66 Illinois

Next we are heading down to St. Louis, Missouri. Don’t forget to subscribe to our blog by entering your email below to follow along on our Route 66 journey!

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6 Responses

  1. Chris travels

    I never had an interest in driving Route 66 as it always sounded unappealing and old school. BUT, your write up and interesting photos have me definately rethinking my logic! Now it’s on my radar and hope to drive at least part if it one day!

  2. Great job with these posts. The breweries looked wonderful. I have to laugh at your Maid-Rite description. Maid-Rites are absolute comfort food for my husband from Iowa. As a kid growing up in Chicago with Iowa born parents we had them but scornfully called them “loose hamburger” sandwiches, assuming my mother was too lazy to make them into patties. Now 35 years with my husband they have regained their true honor as Maid-Rites. LOL

    • That is too funny Janet! We kept rereading the description going, do we really want to stop at this place? But figured we should to at least give it a chance!

  3. terry hudson

    This looks like a fun trip. We travel with a 5th wheel trailer is there any good camping on or near route 66 ?
    Thanks
    Terry

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