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.
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Atlanta is also where you’ll find the iconic 19-foot-tall Paul Bunyon Muffler Man holding a hot dog, one of the most famous statues along Route 66. He’s perpetually standing guard just across from The Palms Grill Cafe.
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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 The I-55/Route 66 shrine was originally made as a high school project.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.”
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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.
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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.
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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.
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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.
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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.
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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.
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If you need one more outdoor adventure before heading into St. Louis, take a short hike around Pere Marquette State Park in Grafton. The park has 8,000 acres perfect for cycling, bird-watching, boating, picnicking, and camping.
Few cities are lucky enough to have an architectural icon like the Gateway Arch overlooking the mighty Mississippi River, but there's so much more to St. Louis. The city has a booming craft brewery scene, a rich history, and top-notch cultural institutions. Whether you're eating at an old-school soda fountain or getting lost in a phantasmagorical wonderland (we’ll explain later), St. Louis is an excellent weekend destination.
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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.
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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.
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Though tiny and unassuming, you won't find a better 24-hour greasy spoon than the Eat-Rite Diner. If you're not sure what to get, order the Slinger: hash browns, your choice of meat, and eggs topped with chili and onions.
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The Lemps were once one of the most influential families in St. Louis. Prohibition, divorce, death, and depression hit them hard, but most of the really dark stuff happened in their stately home known as Lemp Mansion.
William Lemp had been grooming his son, Frederick, to take control of the family grocery business, but the son died at the age of 28 from health complications. Shortly after, William’s friend Frederick Pabst (yes, that Pabst) died. Less than 2 months later, William himself was dead from a self-inflicted gunshot wound; his body was found in the family mansion. Things only got worse from there: Two of William's remaining children also died by suicide and, because of Prohibition, the family’s brewery closed.
William's son Charles continued to live in the house until the 1940s. He never married and was known for his strange behavior. He mailed a letter to a St. Louis funeral home with very specific instructions upon his death: He wanted his remains transported to a crematory by ambulance and cremated immediately; he requested that his body not be bathed, clothed, or altered in any way. He wanted his ashes to be placed in a wicker box and buried on his farm, without a funeral or death notice printed in the papers. Eight years later, he shot his dog and then himself, leaving behind a note saying, “St. Louis Mo/May 9, 1949, In case I am found dead blame it on no one but me. Ch. A. Lemp.”
The ghosts of the Lemp family reportedly still haunt the mansion, now a dinner theater and bed and breakfast. Patrons frequently report seeing William Lemp’s ghost peeking into bathroom stalls in the downstairs women's restroom and claim to have seen a spirit running up the stairs. Others hear horses outside or find that items have mysteriously moved across the room. A doorway in the basement leading to the beer storage caves is referred to as “The Gates of Hell.”
Brave travelers can book a stay in the mansion. If you’re lucky, you might get to meet one of the Lemps and knock back a cold one—with a cold one.
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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.
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.
