I started the day in St. Louis with a strong coffee and a loose plan. With time on my side, I wandered through downtown, where the sculpture gardens offered a calm mix of modern art and green space—an easy stop before hitting the road.

That relaxed start didn’t last long. I quickly realized I had no idea where I’d parked the car the night before. What should have been a quick departure turned into a 30-minute search, eventually ending with help from the police. Not exactly planned—but memorable.

Custard and Caverns

Once I was finally on the road, I made my first stop at Ted Drewes Frozen Custard. It lived up to the hype—thick, ultra-creamy custard with rich ribbons of caramel that made it one of the most indulgent treats of the trip so far.

From there, I headed to Meramec Caverns, a classic Route 66 stop. The guided tour led deep underground through vast chambers filled with towering rock formations and echoing silence. The caverns are also tied to stories of Jesse James—fact or folklore, it adds an extra layer of intrigue to an already impressive experience.

Small Towns, Surprises, and Springfield

With the caverns behind me, the road opened up and the drive began to feel familiar—one of those stretches where everything feels both new and nostalgic at the same time.

I stopped in Cuba, Missouri, known as “Mural City,” where large murals tell stories of local history and Route 66 culture. It’s not a major destination, but it’s a good place to stretch your legs. Not far from there, I passed the World’s Largest Rocking Chair—exactly the kind of quirky landmark that defines this route.

One of the best moments of the day came out of nowhere. Passing through Rolla, Missouri, I stumbled onto a local Route 66 celebration in full swing. Classic cars lined the streets, bands played in the streets and I even got to sit in a beautifully restored 1932 Ford. Those unplanned stops are often the most memorable.

I also made a short detour to Devil’s Elbow Bridge, one of the original stretches of Route 66—still holding onto the spirit of the old road despite the changes around it.

By the time I reached Springfield, Missouri, I was ready to slow down. Known as the “Birthplace of Route 66”, the town was buzzing. The downtown square was alive with music and celebrations marking the 100-year anniversary of the historic route.

That evening, I got talking to a group of locals who told me about a unique Route 66 race happening later in the year—no GPS, just paper maps, strict timing rules, and a lot of navigation skill. Complicated, but fitting for a road like this.

By the end of the day, I’d gone from city streets to underground caverns, across rolling Missouri hills, and into the middle of a Route 66 celebration—a day that started with a missing car and ended in a street full of classic cars!


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