Route 66 in Missouri – Unexpected Highlights and Bizarre Moments

St Louis MIssouri

If you had told me before the start of driving Route 66 that Missouri would include some of my favorite moments of the adventure, I would never have believed you. It’s not that I don’t like Missouri, I do; in fact, I used to live there. But maybe it’s that past experience that led me to believe Route 66 in Missouri would be pro forma – just something that had to be done on the way to better things. Almost immediately though I realized that Missouri would be no ordinary leg of the trip and even today, a few months removed from the Route 66 drive, some of my most vivid memories come from the two days we spent traversing the state. There were many highlights of driving Route 66 in Missouri, oddly enough, but here’s what any through-driver should expect from the experience.

Chain of Rocks and St. Louis

Missouri plays an important role in the history of Route 66 and there are several key spots along the way that figure prominently in Route 66 lore, starting with how one enters the state from Illinois at the historic Chain of Rocks Bridge. Until 1967, this was the preferred method of entering St. Louis for Route 66 drivers since it avoided the congested downtown, but by the 1960s the volume of cars had become too much and the bridge was closed. It sat in disrepair for decades until it was reimagined and today is part of a comprehensive bike and running trail system. St. Louis was also an important stop for me personally because it was here, two years earlier that the idea of driving the entirety of Route 66 came to me.

Thanks to a special exhibit at the Missouri History Museum, I gathered all the information I needed to tackle the drive. I also returned to one of my favorite hotels, the gorgeous Ritz-Carlton, St. Louis where the level of comfort and hospitality is exceptional even among other Ritz-Carlton hotels. It was the perfect home base to spend a brief few hours re-exploring the city and enjoying some much deserved down-time.

Strange Trek Through the Ozarks

This section of the drive was perhaps the most eye-opening for me personally. I just assumed that a vast majority of Route 66 would be through flat farmlands, but that’s not at all the case. In Missouri, we spent most of the time driving through the Ozarks where dense forests, rolling hills and pristine streams defined the topography. It was also the quirkiest day of the entire drive without question. More than just one moment, it was everything that we experienced driving from St. Louis to Springfield that formed one holistic mass of oddness, but in a good way. Visiting one of the world’s largest rocking chairs (but not THE largest), stopping by both the very strange rest stop town of Uranus as well as what has to be the world’s largest gift shop, the day made me laugh randomly and nearly constantly. It was eye opening; it was a part of the US I had never before seen and I learned a lot about my own country. It was everything I had hoped that Route 66 would be and more.


The leg also features more sights critical to the Route 66 story, particularly around a spot known as the Devil’s Elbow. Named for a severe bend in the nearby river, this is one of the oldest sections of Route 66 still in tact and offers a glimpse into what those first drivers must have experienced. The roads leading to it are amongst the oldest highways in the country, originally developed to help transport military personal. The bridge has thankfully been restored and emblazoned with the Route 66 shield and for me, was a highlight of the drive through Missouri.

More Incredible Food

Finding great food was never a challenge on Route 66, but the meals and snacks I enjoyed in Missouri I think were my favorite. It started in St. Louis where I returned to my favorite ice cream place in the country, Ted Drewes, which is actually frozen custard and not ice cream. They’ve been an important fixture on Route 66 for decades and even have a special dessert devoted to it, which I of course had to try. Keeping with the dessert theme, I had made a special note to stop at a small café in Rolla famous for one thing – pie. I’m glad I did too, because the massive slice of pie at “A Slice of Pie” was probably the best I’ve ever had. They’re actually world-famous and every day sell a variety of different pies, all freshly made in the back kitchen. It wasn’t all desserts though, before leaving Springfield we skipped breakfast at our hotel in order to visit a local institution, Gailey’s Breakfast Café. Moving to its current location in the 1940s, Gailey’s has been a critical stop for Route 66 drivers since the day it opened. In fact, Springfield itself is crucial to the Route 66 story, as I learned during my time in this odd but fun city.

Springfield & the Birthplace of Route 66

Springfield isn’t the only spot to lay claim as being the birthplace of Route 66, but theirs is perhaps the strongest argument. A businessman from Springfield joined forces with Cyrus Avery, also known as the Father of Route 66, and mapped out what would become Route 66. In 1925 Congress enacted legislation that made the new highway possible and in 1926, a telegram was sent from Springfield proposing the name for the cross-country route. That’s why Springfield, accurately I think, considers itself to be the birthplace of the Mother Road. Driving into the city was as much fun as the day of driving had been, thanks to a bizarre stretch of road that mostly caters to truckers, but which has some of the quirkiest signs and shops I’ve ever seen. Finally though we arrived to the incredibly comfortable TownePlace Suites, our home for the night. One of the many aspects I loved about partnering with Marriott for the drive was the opportunity to stay at all levels of Marriott brands. I was very impressed not only by the comfort at the TownePlace Suites, but all of the amenities, including a new restaurant featuring progressive, modern and delicious dishes.

We devoted the next morning to exploring Springfield and visiting those spots important to the Route 66 story, including Gailey’s for breakfast as well as walking around downtown, tracing the various alignments Route 66 has taken over the years. Before leaving town, we stopped at the Route 66 Information Center to learn more about the Route in Springfield as well as to get some tips for the next leg of the trip. It was here where we learned about the quirky roadside stop everyone has to visit, Gary’s Gay Parita, as well as the Birthplace of Route 66 Roadside Park. Springfield impressed me a lot more than I thought it would and to be honest, I’d like to return and do a little more exploration.

Route 66 Missouri Gary's Gay Parita

Carthage Missouri


Missouri was the unexpected highlight of Route 66 for both myself and my driving partner, pro-photographer and YouTube personality Brendan Van Son. It was here where he uttered the quote of the trip, “I feel like we’re nowhere and everywhere at the same time,” which for me defined the entire two week experience. Missouri introduced me to a part of the country I didn’t know about and to people unfamiliar. But I loved every second of my time crossing the state and I honestly think it’s one of the shining stars of the Route 66 experience.


This post was created in partnership with Marriott International, but all thoughts and opinions are entirely my own.

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

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