Route 66 Leg One: Chicago to St. Louis

Atlanta is also home to the Route 66 Arcade Museum, a fantastic hidden gem. It features a collection of vintage arcade machines (made between 1934 and 1982) that you can still play for just a quarter.

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.

After visiting Paul Bunyon and his hot dog, head over to the town of Lincoln to check out one of its more bizarre presidential monuments—a statue of a two-foot-long watermelon. In 1853, before he was president, Abraham Lincoln visited the town during its naming celebration. He grabbed a watermelon from a nearby stand, juiced it, and then gave a speech. More than 100 years later, in 1964, the town erected this delicious piece of historic kitsch to commemorate the occasion.

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.

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.

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 The I-55/Route 66 shrine was originally made as a high school project.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.”

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.

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.

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.

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.

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.

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.

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.

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.