Route 66 in Illinois – Meeting Giants and Eating Shoes

Pontiac Illinois

Any great adventure, no matter how momentous, has a beginning and for Route 66 that’s in Illinois. Actually, to be factually correct, Chicago can either serve as the start or the end of Route 66, but for my adventure I decided to start in what is the traditional beginning of The Mother Road. This is the same directional progress of those millions who came before me, whether Dust Bowl refugees heading to California for a better life or their descendants who used the same road to explore the country and maybe even visit Disneyland. I don’t think that the first half of Route 66 gets nearly as much attention as it deserves, and part of that is understandable. It’s not the American Southwest with its iconic desert landscapes and flashing neon signs. But the spirit of Route 66 is very much alive in states like Illinois, which perhaps may embrace the road more than any other state. With that in mind, I want to share what I think are some of the key moments of tackling Route 66 in Illinois and how those experiences help form the ideal beginning for this driving marathon.


November 11, 1926 – that’s when Route 66 was born in Chicago, another reason why the Windy City makes for the ideal start to the trip. Route 66 was realigned a few times over the years, so there are two different spots in Chicago where you can start the drive. In 1926, the road began at Jackson Boulevard and Michigan Avenue but then in 1933 the start was moved a few blocks away. Today the Route 66 Begin sign is on the corner of Adams and Michigan and can be a little hard to miss, so keep your eyes open. Before you start heading down the Mother Road though, be sure to spend some time exploring what is truly one of the country’s great cities. Since it was my first time playing tourist in the city, I had a list of key sights I wanted to visit. Arriving into Chicago, I first checked into the newly opened Marriott Marquis Chicago, a beautiful hotel that has some of the best design and style elements I’ve ever seen. It’s also a great home base to see the best of the Windy City. Grant Park, the Willis Tower and of course the famous Architectural River Cruise all formed the base of my explorations and helped me finally learn to enjoy the city. Don’t spend too much time in the city though, there’s a lot more to see throughout Route 66 in Illinois.


We weren’t on the road for very long when it was suddenly time for our very first stop on the 2,400-mile drive and our first of many Route 66 museums. Even before reaching downtown Joliet though, Route 66 imagery popped up everywhere and it immediately became apparent that not only Joliet, but the entire state warmly embraces its Route 66 legacy. Parking next to one of the many Route 66 interpretative signs in town, I walked across the street to the Joliet Area Historical Museum that, while strongly promoting Route 66, highlights the area’s rich history just as ably. From the Blues Brothers to the Mother Road, the city has an oddly important place in pop culture, all of which you can learn about here. Joliet is also the ideal first stop because of just how strong the spirit of Route 66 is felt around town. We met other folks who, like us, were just starting the grand adventure and it was wonderful to spend some time chatting with them, all of us excited for the journey ahead.



Advertising imagery plays an incredibly important role along Route 66 from those famous neon signs to the old Burma Shave slogans and yes, even giants. The goal of small business along Route 66 was to get people to stop, and what better way than by offering a roadside attraction? For many spots this took the form of giant structures, including two in Illinois that are now famous – the Gemini Giant and Paul Bunyan. At around 20 feet tall, the Gemini Giant is one of Route 66’s most recognizable giants and this advertisement for mufflers reflects the country’s obsession with the space program. It stands next to the equally famous (and kitschy) Launching Pad Drive-In, which has just been reopened by new owners. In Atlanta, Illinois we found another muffler giant, Paul Bunyan. Holding a hot dog instead of an ax, he was relocated here after the town won a bid for this 19-foot giant.

Classic Eats

As one would imagine, food plays an important role along Route 66, those regional favorites remaining unchanged for decades. While the Route 66 shield themed pork tenderloin I enjoyed at the Old Log Cabin Inn in Pontiac was delicious, what I know I’ll never forget is my introduction to the horseshoe sandwich. At Weezy’s Route 66 Bar & Grill in Hamel I found an explosion of kitsch, but don’t let that get in the way of the food. This is a classic diner and one of the most popular meals is also an Illinois classic, the ‘shoes. On an enormous platter slices of bread, meat, French fries and a thick cheese sauce are layered, creating a unique concoction that exists somewhere between the Welsh rarebit and poutine. It’s also, naturally, delicious. The traditional horseshoe though is enormous, but thankfully at Weezy’s they offer a smaller version – the pony shoe, which was more than enough food for a lunch on the go.

Springfield Illinois

Land of Lincoln

Spending the night at the imminently comfortable Residence Inn in Springfield, it was also a great opportunity to explore this beautiful state capital. If you have any interest in the life of Abraham Lincoln then this is your place, with more than enough to fill a few days of exploration. I was drawn immediately though to the gorgeous Old State Capitol building. Built in the 1840s, it’s not just beautiful but has played an oddly important role in history, including in the life and times of Lincoln. No matter your interests, just be sure to spend a little time exploring Springfield before continuing on Route 66.

Quirky Towns

A feature that endears Route 66 to millions around the world isn’t visiting the large cities along the way, it’s the small quirky towns and Illinois has them in abundance. Many of these towns have certainly seen better times, whether from the loss of industry or the traffic that roads like Route 66 once brought into town. A favorite for many is Pontiac, thanks entirely to the town’s clear love of Route 66. It’s where we found the Route 66 Association Hall of Fame and Museum; a quirky space that pays tributes to the many people over the years who have all had a role in making Route 66 the important historic time capsule that it is today. Not to be missed though is the enormous mural on the back of the building – the ideal spot for those Instagram photos. Towanda, Illinois has created a Route 66 Park and Restoration Project and in Atlanta you’ll find a small park and many Route 66 inspired businesses that still attract curious passersby. The one quirky stop in Illinois that we didn’t manage to fully enjoy was Henry’s Rabbit Ranch. Closed when we arrived, the ranch is actually in an old filling station and it’s here where you can spend some time playing with the many rabbits that call this place home. No matter which of the many quirky towns you decide to visit, they are important features of the drive and just can’t be missed.

Route 66 Matt Illinois

Illinois Embraces the Route

Looking back at the entirety of the drive, I know now that Illinois embraces Route 66 perhaps more so than any other state. The Route is very clearly marked throughout the state and most of the small towns along the way have some sort of tribute to Route 66. I wish I could say that’s a common feature throughout the country, but it’s not and makes Illinois an important piece of the overall drive. It’s also important since it’s where so many people start the drive, and Illinois has made those first few days easy and fun, setting the tone for the rest of the drive.

Route 66 is dependent on all of the states through which it runs, and not just those few whose landscapes have helped them become more prominent in pop culture. Route 66 is also about connecting with the country on a very different level and in a very different way, and Route 66 in Illinois is perhaps one of the best sections to quickly see just why the Mother Road has remained in our national consciousness for so very long.


This post was created in partnership with Marriott International, but all thoughts and opinions are entirely my own.

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

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