The stretch of Route 66 from Chicago, Illinois, to St. Louis, Missouri, is home to aluminum-and-chrome diners, historic, family-owned cafes, bizarre attractions, and other reminders of the route’s charming past. You’ll also see plenty of cornfields and flat prairie land between the bustling cities and sleepy towns along this first leg.
The Illinois stretch of Route 66 is home to several great roadside attractions, but nothing shouts "retro kitsch" louder than a massive Muffler Man. Snap a picture with the Gemini Giant the newly-reopened Launching Pad Drive-In in Wilmington. Named for the Gemini space program, he’s one of many similar statues made by International Fiberglass. The giant stands guard over the Launching Pad Drive-in, which also houses a gift shop, a restaurant, and the Mini Americana Museum.
The Shrine of Our Lady of the Highways has been watching over travelers since the 1950s. The I-55/Route 66 shrine was originally made as a high school project. Stop at this beautiful roadside stop to pay homage to our guardian of asphalt, represented here by a statue bearing the inscription “Mary, Loving Mother of Jesus, Protect us on the Highway.”
Thought to be one of the first restaurants on Route 66, Litchfield’s Ariston Cafe is a roadside icon. Founded by Greek immigrant Pete Adam in 1924 (and moved to its current location in 1935), the cafe was placed on the National Register of Historic Places in 2006. The Adam family has been running the place for years, and the desserts are just as rich as the history.
Located just 10 to 15 minutes down the road from Ariston Cafe, the Soulsby Station was designed and built in 1926 by Henry Soulsby. The building was designed to blend in with the surrounding residential area. Today, the station has been beautifully restored and is a popular stop for Route 66 travelers.
Six miles south of Mount Olive, take a slight detour to Henry's Rabbit Ranch in Staunton. The ranch is full of Rabbits—both the Volkswagen kind (some stick out of the ground in a Stonehenge-like fashion) and the fluffy kind. If you’re lucky, you might get to meet the owner and pet the real-life rabbits that spend their days hopping around the store. A short drive away is the St. Paul Lutheran Church and its large blue neon cross.
Pink Elephant Antiques is a treasure trove of quirky roadside attractions all in one place. Here you’ll find vintage neon signage, fiberglass giants, and lots of other weird stuff. There’s a cone-shaped ice cream stand, a UFO-shaped 1960s Futuro House, and—fittingly—a huge pink elephant. While there, stop at the on-site flea market, where you could easily spend several hours. For a bite to eat, hit up Weezy’s Bar and Grill in nearby Hamel.
But wait—there are two more essential roadside stops before you leave Illinois: the World’s Largest Catsup Bottle and the Cahokia Mounds. Originally built in 1949, the catsup bottle is an excellent example of roadside Americana, and thanks to a preservation group, it stands as tall and beautiful today as it did 70 years ago.
Cahokia Mounds State Historic Site was once a heavily populated city that covered 6 square miles. Today, it clocks in at nearly 3.5 square miles, with 80 of the original 120 mounds remaining. This was the largest pre-Columbian settlement north of Mexico, and no other North American city surpassed it in size until the 1800s. Visitors can see the resting place of an important ruler (housed in Mound 72), a Cahokian version of Stonehenge (but with wooden poles instead of giant stones), and the public plaza, where Cahokians played a highly competitive moving-target, spear-throwing game called Chunkey.
Your last food and drink stop in Illinois should be Luna Cafe. Built in 1924, this Route 66 roadside joint was a favorite hangout and hideout for Al Capone. The neon sign alone is worth a visit, but the cold beer and good food make Luna the perfect place to stop before continuing into Missouri. The Luna Cafe is nothing fancy, but that’s part of its appeal.
200 South Broadway, St. Louis, Missouri
Gateway Arch National Park is so much more than just the iconic arch. There’s also a free museum with exhibits detailing U.S.’s westward expansion and the building of the Gateway Arch, which is a good place to start if you’re waiting for your ride to the top (or if you’re scared of heights but still want the arch experience). A trip to the top of the Eero Saarinen-designed monument—the world’s tallest arch and the tallest man-made monument in the U.S.—offers great views of both sides of the Mississippi. Across the street is the Old Courthouse, site of the Dred Scott trial, which features an ornately decorated dome.
If you're in the mood for classic American grub, then stop by the historic Crown Candy Kitchen for some sweets and a classic counter lunch of sandwiches. The BLTs here are the stuff of legend, but the milkshakes are the real draw—you can’t go wrong with a hot fudge or chocolate banana malted.
The St. Louis Soldiers Memorial Military Museum was originally built to honor local citizens who lost their lives in World War I. This a sobering and well-thought-out museum that includes uniforms, weapons, portraits, and art installations.
City Museum describes itself as a “phantasmagorical wonderland.” Opened in 1997, the museum, housed in an old shoe warehouse, contains found architectural and industrial objects—including a school bus, cranes, a fire engine, and two old Saber F-86F aircraft fuselages. There’s also an aquarium, a Ferris wheel, and a 10-story slide, but don’t expect to have an easy time finding any of it. The whole place is a maze of exhibits—and there are no maps. Visitors are encouraged to explore and discover on their own. You never know where a ladder or slide will take you— you could end up inside a life-size whale statue, at a giant skate park, in an enormous pit filled with dodgeballs, or in a treehouse bar.
St. Louis Union Station looks like a castle, but it's actually a converted rail station. The building is stunning, inside and out—seriously, the lobby is drool-worthy. Inside is an aquarium, a variety of dining options (including a soda fountain that makes over-the-top shakes), a mini golf course, and much more. If you’re not ready to leave, you can book a room at the St. Louis Union Station Hotel. Don’t miss the hourly light show, projected onto the 65-foot vaulted ceilings each night between 5 p.m. and 10 p.m.
St. Louis loves its barbecue, and Pappy's Smokehouse is one of the city's most beloved BBQ joints. The restaurant only serves food until it runs out—and the wait might be long—but once you taste the ribs or burnt ends, you'll understand why. There’s also Frito pie, which includes cheddar cheese, baked beans, your choice of meat, and onions over a pile of Fritos. Sounds weird, but trust us, it's totally delicious.
Ted Drewes Frozen Custard, a Route 66 icon, has been serving hot and hungry road travelers for more than 80 years. After opening his first successful custard store in Florida in 1929, Drewes opened a few more stores, including this stand located on Historic Route 66. Almost a century later, the stand is still a family-run business.
You did it—one leg down, five more to go. As you travel further southwest, the weather will get warmer, the road will get flatter, and the views will only get better. While it’s true that you never forget your first, so much of Route 66 is still in front of you—so keep going and let the Show-Me State show you why almost 100 years after its creation, the Mother Road is still the best place to get your kicks.