Route 66 Leg One: Chicago to St. Louis

If you plan on starting your Route 66 adventure in Chicago, this is the perfect campground for tenting, RVing, or cabin camping. The South Shore Line offers rail service directly from the state park to downtown Chicago.

Don’t miss the Route 66 Starts Here sign at the corner of S Michigan Avenue and E Adams Street. The sign (along with a handful of replica signs on the same block) is located in a busy section, so you may need to find parking elsewhere and walk to the sign for a photo.

Chicago's landmark is considered one of the country's finest fountains due to its Beaux-Arts-style landscape design, finely wrought bronze sculpture, and innovative use of technology.

It's one of the first stops Ferris Bueller makes on his day off, so you know it's an essential Chicago icon. The Skydeck really does offer great views when the weather is good, plus the glass-floored "ledge" is an unforgettable experience for those brave enough to step on to it.

The Route 66 Association Hall of Fame and Museum is full of fascinating, family-friendly exhibits, and the staff’s love of the route is infectious. Don’t miss the wall art and wishing well in the museum’s backyard.

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.

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.

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.

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.

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.

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.