Route 66 Rev Leg 6: St. Louis to Chicago

On your way out of St. Louis, hit up the sprawling Laumeier Sculpture Park and Museum. Stretch your legs among the weird and wild outdoor art exhibits, which include a gigantic eyeball in the middle of a field.

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.

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.

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.

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.

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.

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.”

For the full Lincoln experience, spend the night at the Pasfield House Inn in Springfield. This gorgeous bed and breakfast is owned and operated by Tony Leone, a local historian, who greets his guests with that famous Prairie State hospitality. The Georgian-style inn is a Springfield landmark, and oozes with style.

The home was built in 1896 and has been lovingly preserved under the care of Leone since 1996. The six-suite bed and breakfast sees quite a lot of visitors, especially history buffs on Lincoln-inspired pilgrimages.

George Pasfield was a banker who met Lincoln when they both lived in Springfield. Pasfield and Lincoln were both involved in establishing the state capital in Springfield. As the patriarch of one of the wealthiest families in Springfield, Pasfield owned acres upon acres of land around the State Capitol.

The inn is within walking distance of the Illinois State Capitol and downtown Springfield. It is also close to the Cozy Dog (corn dogs and french fries are a totally acceptable breakfast). If you have time, reserve a spot on the spirited 90-minute, 10-block Lincoln Ghost Walk Tour. Springfield has a little something for everyone: History buffs, Route 66 aficionados, and foodies will all find something to love in the Land of Lincoln.

If you’re in the mood for a food challenge, head over to Joe Rogers’ Chili Parlour and partake in the Firebrand Chili Challenge. See how many bowls of the famous extra-spicy chili you can eat—the current record is five.

At Obed & Isaac’s you’ll find one of the more bizarre culinary confections that Illinois has to offer. The Horseshoe Sandwich is made with two slices of toast (usually Texas-style), piled high with two burger patties, fries, and cheese sauce. A side order of seasoned fries is a must.

While the corn dog technically wasn’t invented here, the Cozy Dog Drive In claims to be where it was first put on a stick. Stop by to taste the original “Cozy Dog” and don’t forget to take a photo of it in front of the vintage sign.

In 1837, the Springfield Road was constructed to connect St. Louis with Springfield, Illinois. The route became a popular stagecoach line for the next 20 years, but with the rise of the railroad, roads like this fell into disuse and disrepair. The advent of the automobile provided a welcome comeback and by 1920, there were tens of thousands of cars on the road.

In 1925, the American Association of State Highway Officials approved a marking system for interstate highway routes. East-west routes were designated with even numbers and they all ended with a “0”—with one exception. After some controversy, mainly on the part of delegates from Kentucky, the route from Chicago to Los Angeles, California, was given the number 66.

As the name suggests, the town of Lincoln has a bit of an obsession with the 16th president of the United States. The almost 25-foot-tall Railsplitter Covered Wagon—the world’s largest covered wagon—is no exception. Today, it sits on the front lawn of a Best Western hotel, and Abe himself can be found sitting on the wagon reading a law book.

For travelers with a sweet tooth, Funks Grove Pure Maple Sirup in Shirley is a must-see (and must-taste). Funks Grove produces more than 2,000 gallons of maple syrup—or “sirup”— per year using old-fashioned sap-gathering techniques. The finished product comes in beautifully designed bottles.

The route is dotted with old service stations, many of which have been beautifully restored and repurposed as photo ops. The first one you’ll encounter is Ambler's Texaco Gas Station in Dwight. In continuous use for 66 years, from 1933 until 1999, it was one of the longest operating gas stations on the Mother Road. Today it serves as a visitor center.