Missouri Road Trip to Kansas City: Day 1

Friday morning I woke up in Chicago at 5am and was out the door around 5:45 on my way to Urbana, Illinois. I picked up my friend Brian at around 7am and we hit the road together. It was time for our Missouri Road Trip to Kansas City!

Our three day Missouri road trip was taking us from Chicago to Kansas City, Missouri (but technically Overland Park, Kansas), and we had lots of stops at fun roadside attractions, iconic hamburger restaurants, and even an eating contest on our itinerary!

Our first and only stop in Illinois was the World’s Largest Catsup Bottle in Collinsville. I’d seen it before, but as ketchup is probably one of my favorite inventions ever, it is probably one of my favorite roadside attractions ever. Brian had never seen this particular tourist trap and remarked that it would be more impressive if it was actually filled with ketchup. And I agree. But I love it none the less. After taking some photos of the giant condiment, it was off to St. Louis!

Honestly I don’t think I have ever even been to Missouri before! So it was exciting to navigate through the highway and drive by the famous arches into brand new territory.

While St. Louis seems to be a treasure trove of awesomeness, we didn’t make any stops at attractions there. We had a lot more ground to cover and I figure I just have to go back to experience the City Museum (a stop we certainly had no time to take) so I will explore that area another time.

We did stop for lunch at Sweetie Pie’s, a soul food kitchen that was once featured on the Food Network TV show Diners, Drive-Ins, and Dives. I filled my stomach with tangy smothered pork and creamy mashed potatoes and was contented in the warm hospitality the place displayed.

Smothered pork and mashed potatoes at Sweetie Pie's in St. Louis, Missouri.
Smothered pork and mashed potatoes at Sweetie Pie’s in St. Louis, Missouri.

After lunch, we decided to move on from St. Louis. Navigating city traffic always puts you a little behind and we had so much else to see on our Missouri road trip to Kansas City.

We went to Clayton next to see a giant shoe made from shoes and then Columbia to see a statue of Beetle Bailey. We were on a renegade mission, putting dimes into parking meters and running to take photos and bask in the awesomeness of everything just to get back to the car as the meter was about to expire. A girl was studying at the Beetle Bailey statue and I didn’t want to ask her to move so I tried photographing around her.

Next on our road trip in Missouri, we headed to Sedalia, where we saw Katy Depot, a neat little museum devoted to the area’s railroad industry, complete with some cool artwork on the railroad itself!

While in Sedalia we made a stop for lunch #2 of the day, The Wheel Inn, and partook in their claim-to-fame specialty: The Guberburger. The Guberburger is a hamburger topped with lettuce, tomato, and…wait for it…peanut butter! It was quite tasty and all in all I was much more surprised that I ate a burger with lettuce on it than that I ate a burger with peanut butter on it!

Katy Depot - Sedalia, Missouri's Welcome Center and Museum
Katy Depot – Sedalia, Missouri’s Welcome Center and Museum

After filling our stomachs yet again we hit some back roads to see two world’s largest things: the world’s largest pecan in Brunswick and the world’s largest goose in Sumner! The pecan was cool and the goose was amazing! It was one huge bird!

Our final Missouri roadside attractions stop of the the first day was Chillicothe. Have you ever said that something was the greatest invention since sliced bread? Well, you have Chillicothe, Missouri to thank for that as it is the home of sliced bread!

From there we hit the road to Overland Park, Kansas, completing the first leg of our Missouri road trip to Kansas City, where we had a hotel for the night.

We were going to just order a pizza from the room, as we were pretty tired and wanted to get to blogging! But, low and behold, what was right outside our hotel? A Winstead’s! Winstead’s is a hamburger joint that was named one of the best burgers by George Motz in his book Hamburger America. Luckily it was still open for another hour so we got some burgers and shakes and fries AND onion ring before heading to the hotel to retire for the night and get ready for the second day of our Missouri road trip and the big hot dog eating contest ahead!

Missouri Road Trip Log:

Day 1: Road Trip to Kansas City
Day 2: Missouri Hot Dog Eating Qualifying Contest
Day 2: Kansas City Roadside Attractions
Day 3: Heading Home
Video Recap

Valerie Bromann

Founder & ROad Trip Expert

Valerie Bromann is a a website manager, content creator, and writer from Chicago, Illinois (currently living in Dallas, Texas). As an avid road tripper who has visited hundreds of roadside attractions, Val always pull over for a world’s largest thing. Founder of Silly America and author of The Road Trip Journal & Activity Book, she visits, photographs, and writes about all the weird tourist destinations she visits and offers road trip planning advice and inspiration based on her own travels so you can hit the road for yourself.

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Last modified: November 15, 2023
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The Road Trip Journal & Activity Book - Everything You Need to Have and Record an Epic Road Trip! By Valerie Bromann

The Road Trip Journal & Activity Book

Everything You Need to Have and Record an Epic Road Trip!

BY Valerie Bromann

Enjoy fun games and challenges to pass the time on your next road trip and have a keepsake to look back on for years to come with this entertaining must-have for your next vacation.

The road trip you’ve been dreaming of starts here! Journal about your stops and get to know your fellow passengers with activities and exercises designed to pass the time and bring you closer together. Instead of “Are we there yet?” you’ll find yourself asking, “We’re there already?”. Complete with prompts you can turn to while driving between locations, this journal will one day be a memento of your life-changing trip.