Entering Missouri – St. Louis & Surrounds

 

Crossing the Mississippi into Missouri, the excitement of Route 66 is palpable. Your first taste of the Mother Road in the Show-Me State starts with the Old Chain of Rocks Bridge, a historic marvel with its distinctive 22-degree bend. Walking or cycling across this bridge feels like stepping back in time — imagine Model Ts rattling along the metal frame a century ago. With panoramic views of the Mississippi River on one side and St. Louis on the other, it’s the perfect introduction to Missouri’s Route 66. Don’t forget to snap a photo of the graffiti-covered entrance — a quirky touch that adds character to this historic crossing.

 

From there, it’s a short drive into St. Louis, where the city balances big-city thrills with Route 66 nostalgia. Start with the iconic Gateway Arch, a gleaming monument that’s both a symbol of westward expansion and a perfect photo opportunity. Then, follow your nose (and sweet tooth) to Ted Drewes Frozen Custard, a local institution serving up creamy, indulgent treats that might just become the highlight of your day. Car enthusiasts will want to swing by the St. Louis Car Museum, a hidden gem full of vintage beauties that celebrate America’s automotive history.

 

As you leave St. Louis, you’ll feel like you’ve had a proper Route 66 welcome: a blend of history, quirky attractions and that unmistakable open-road excitement. Keep your camera ready — the journey through Missouri is only getting more colourful.

 

 

Central Missouri Gems – Sullivan, Cuba & Saint Robert

 

Heading west, Route 66 leads you to Sullivan, where the underground wonders of Meramec Caverns await. These glittering limestone caves are more than a natural spectacle; they’re steeped in legend, with tales of Jesse James possibly hiding in their shadowy corridors. Guided tours weave together geology, folklore and a touch of drama — perfect for both kids and adults. It’s the kind of roadside attraction that makes you feel like an explorer discovering a hidden world.

 

Next, roll into the charming town of Cuba, known as the “Route 66 Mural City.” The streets here are alive with outdoor murals, each one telling a story of the Mother Road and Missouri life. It’s essentially an open-air art gallery, perfect for selfies and photography enthusiasts. While wandering, be sure to stop at the Wagon Wheel Motel, a vintage roadside gem that still serves classic travellers and grab a bite at Missouri Hick Bar-B-Q — the smoky aroma alone is worth the stop.

 

Just a short drive later, you’ll reach Saint Robert, home to the Route 66 Neon Park. Rows of revitalised neon signs light up the past, showcasing the glitz and charm of mid-century America. Walking through the park feels like stepping into a roadside postcard and it’s a perfect opportunity to capture some of the most Instagram-worthy shots on your journey. Central Missouri truly delivers on the quirky, colourful character that makes Route 66 unforgettable.

 

 

Lebanon & Springfield – Classic Route 66 Heartland

As you head deeper into Missouri, the Mother Road reveals its heartland. Lebanon is a must-stop for nostalgia lovers, where the spirit of classic Route 66 lives on. The Route 66 Museum is a self-guided treasure trove of vintage diners, classic gas stations, and memorabilia — offering a vivid slice of life from a bygone era. Just down the road, you’ll find the Munger Moss Motel, one of the most photographed icons on Route 66. While you can no longer stay overnight, the property remains open for visitors to admire and snap photos of its famous neon sign and charming mid-century façade.

From Lebanon, your journey continues to Springfield, proudly known as the birthplace of Route 66. This city isn’t just a historical footnote — it’s alive with culture and attractions. Visit the History Museum on the Square to dive deeper into both local history and the story of the Mother Road. Springfield is also home to some of the biggest centennial events in 2026, so you might catch a car show, parade, or live music while you’re there. The streets are lively, the cafés welcoming and the Route 66 spirit palpable in every corner.

Springfield marks a significant milestone on your trip: the city where the route’s name was officially decided. Standing here, you can almost feel the energy of road-trippers past and present, a perfect pause before heading toward Missouri’s western frontier.

 

 

Western Missouri Finale – Ash Grove, Carthage & Joplin

Continuing west, Route 66 takes you to Ash Grove, home to Gary's Gay Parita, a charming recreation of a Sinclair gas station from the 1950s. Pull up, and you’re likely to be greeted personally by Barbara, Gary’s daughter, and her husband — both of whom carry on the family tradition of welcoming travellers with genuine warmth and a big smile. It’s this kind of hospitality that makes the Mother Road so special. As you wander among the vintage pumps, signs, and memorabilia, it’s easy to imagine the roar of classic cars and the excitement of mid-century road trips.

Next, Carthage greets you with a double dose of nostalgia. The Boots Court Motel still welcomes travellers with retro charm and nearby, the 66 Drive-In Theatre lets you experience a movie under the stars — a true slice of Americana. Even a quick stop here feels like stepping into a scene from a vintage road-trip movie.

Finally, your Missouri journey concludes in Joplin, where the Route 66 Mural Park and visitor centre make for a celebratory finale. Colourful murals, local history and cheerful townsfolk send you off with a warm goodbye from Missouri, leaving memories and photos that will last a lifetime. Whether you’ve spent a few days or a week exploring, Joplin provides the perfect punctuation to your Route 66 adventure through the Show-Me State.