Route 66 Leg One: Chicago to St. Louis

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.

End your trip through St. Louis at one of the more famous craft breweries in town: the Schlafly Tap Room. In addition to pub food and delicious beers (try the grapefruit IPA or the oatmeal stout), the taproom offers live music Thursday through Saturday.

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.

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.

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.

Whether or not Budweiser is your beer of choice, there's no denying that its operation is impressive. Stop by the St. Louis Anheuser-Busch brewery and take one of the tours. Visitors can enjoy the General Brewery Tour, Beermaster Tour, or The Day Fresh Tour, where guests meet the Budweiser Clydesdales. Or, just grab a brew in the beer garden.

Nothing like a hearty brunch to start your day. Rooster offers a little something for every kind of brunch-lover: traditional scrambles, sweet and savory crepes, French toast topped with caramelized bananas and nuts, and even a brunch burger.

Alternatively, you could check into the Moonrise Hotel, a funky boutique hotel with a galactic theme that promises to take guests on “a journey through space and time."

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.

Wash down your Gioia’s Deli hot salami with a beer—or two—at Dressel's Public House. With an impressive selection of craft beers, wine, and cocktails, this Welsh pub is a cozy place featuring rustic-chic decor and farm-to-table bar bites.

St. Louis’ Italian neighborhood is known as The Hill, and one of the most popular spots in the area is the James Beard award-winning Gioia’s Deli. It has been open since 1918 (with a storefront claimed to be built with brick and wood from the 1904 World’s Fair) and people still line up out the door for the incredible sandwiches. Most of the people in line will probably be ordering the hot salami (or the Salam de Testa, as it’s sometimes called). The salami—hot in temperature, not spice—is made fresh daily and is absolutely worth the wait. Make sure to top it with ooey, gooey, melted Provel cheese (a St. Louis specialty made of cheddar, Swiss, and provolone) and giardiniera (Italian relish).

The Cheshire is a British-themed hotel that may look out of place in St. Louis, but it’s been a fixture in the city for close to a century. Dating back to the 1920s, the Cheshire is a charming throwback to traditional British inns, complete with a cozy on-site pub. A massive taxidermy bear, dark wood furniture, and wall tapestries greet you when you first walk in. A hot tip is to book the James Bond Suite.

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.

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.

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.

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.

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 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.

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.