How to Spend 3 Days Traveling Route 66 in Missouri

Posted: 12/19/23 | December 19th, 2023

A lot of people assume you need to travel abroad to have transformative travel experiences, but that’s simply not true. In this guest post, Raimee Iacofano, my former creative director and creator behind RaimeeTravel, shares how a road trip across one of the most underrated American states can show you a whole new world.

This year I had a big goal: to get outside of my international travel bubble and explore more of my home country, the United States! After years of going abroad every time I had some time off, I wanted to switch things up a bit and prioritize destinations closer to home that weren’t necessarily on my radar.

Thanks to the folks at Visit Missouri, I was able to turn that dream into reality on an extravaganza down the historic Route 66!

This iconic historic highway stretches from Chicago, Illinois, to Santa Monica, California. It gained fame as a major path for travelers, serving as a key route for migration west during the 20th century, and has since become a symbol of American freedom and adventure.

To my surprise, I discovered more than the sprawling highways and flat farmland people tend to think about when it comes to the Midwest (and I’m from Michigan, so I know people don’t typically think of our region as a fun getaway destination!).

On this three-day itinerary, you’ll experience the best things to see and do across Missouri, like massive caves, lush parks, and the kind of quirky road stops I can’t imagine finding anywhere else.

Here’s how to spend three days along Route 66 from St. Louis to Springfield:

Missouri Route 66 Road Trip Itinerary: Day 1

National Museum of Transportation
This museum has an extensive collection of transportation vehicles, including planes, trains, automobiles, and trolleys. You’ll find the types of retro cars you only really get to see in movies and vintage planes that make you question all laws of physics.

My favorite thing in this museum was the Virgin Hyperloop, which is essentially a tube intended to move cargo at airline speeds but at a fraction of the cost, suspended by magnetic systems in a vacuum tube.

Even though the Hyperloop might not ever actually get made for use by passengers (which is totally fine by me, because it seems slightly terrifying), it’s fascinating to imagine and learn about what the future of transportation could look like.

2933 Barrett Station Rd., St. Louis. Open daily 9am-4pm. Admission is $15 ($6 for kids, $12 for seniors).

Meramec Caverns

I had no idea Missouri was also known as “the Cave State,” but this was just one of many surprising things I learned along this road trip. There are actually over 6,400 caves throughout Missouri, and the largest system is Meramec Caverns.

On a 45-minute guided tour, you’ll get to explore and learn about millions of years’ worth of dramatic formations. Plus, you’ll also see the caves lit in beautiful colors, during the unique light show and grand finale. It’s the perfect family-friendly activity.

1135 Hwy. W, Sullivan. Tours run 9am-4pm. Admissions is $27 ($14 for kids).

Missouri Hick Bar-B-Que
A road trip in Missouri would be incomplete without some barbecue, so you’ll want to take a pit stop at Missouri Hick Bar-B-Que before wrapping up the day. This highly rated restaurant feels like walking into a giant log cabin where all your friends happen to be dining. Get the sample platter to try the mouth-watering mac ‘n’ cheese, pulled pork, ribs, and more.

913 E. Washington Blvd., Cuba. Open daily 11am–9pm.

If you have more time to spend exploring (and eating), some additional stops along this leg of the route include:

• Hi-Pointe Drive-In – This is an iconic spot serving burgers and sandwiches with locally sourced ingredients. You’ll feel like you’re in a 1960s diner. Get the sweet potato tots!
• Egg @ Midtown – Super cute breakfast spot with delicious breakfast tacos, shrimp & grits, and other unique dishes.
• Ted Drewes Frozen Custard – Known for its “concrete” custard, Ted Drewes (various locations) has over 80 years of serving frozen custard. I got the strawberry shortcake, and I’m still thinking about it.
• Big Chief Roadhouse – This historic restaurant dating back to 1929 offers a glimpse into Route 66’s past. Plus, you’ll be able to enjoy the delicious, locally sourced, in-house-made American fare while watching sports!

Accommodation: Wagon Wheel Motel
After a long day of driving and exploring, Wagon Wheel Motel is a wonderful place to stay before your second day on the road! The Ozark stone buildings with the original wooden doors, windows, and floors from the 1930s have been updated for modern comfort and convenience. You can’t miss the famous Wagon Wheel neon sign as you drive up to check in!

Missouri Route 66 Road Trip Itinerary: Day 2

Shelly’s Route 66 Café
For some authentic diner vibes and amazing biscuits and gravy, I highly recommend grabbing breakfast at Shelly’s on your way out of town! I have a thing for diner coffee, and Shelly’s did not disappoint. This tiny spot, with its Route 66–themed decor covering every inch of the walls, will make you feel like you’re in on a local secret, and the food will assure you that you are.

402 E. Washington Blvd., Cuba. Open daily 6am–2pm.

Fanning 66 Outpost
Missouri has a lot of interesting “claims to fame,” and being home to the world’s largest rocking chair is one of them. Constructed in 2008, it stands at a towering 42 feet and weighs around 27,500 pounds. There’s really no purpose to it other than being a quirky attraction for tourists and travelers passing through the area.

The Fanning 66 Outpost is also a great place to grab some snacks for the rest of your road trip or a souvenir or two. Say hi to the adorable orange tabby cat for me!

5957 State Hwy. ZZ, Cuba. Open daily 8am–5pm.

St. James Winery
This is Missouri’s largest and most award-winning wine producer, where you can get a free tasting flight! I opted for the dry red and white tasting and really enjoyed it. The staff here was lovely, and the entire shop was decorated for the holiday season. I actually won a candle in the holiday raffle — and I never win anything!

540 State Rte. B, St James. The tasting room is open daily 8am–6pm.

Sybill’s Restaurant

This elegant, country-style manor turned restaurant is one of Missouri’s best fine-dining experiences. Unlike other such places, the atmosphere here is very family oriented, unstuffy, and welcoming! If you get the chance to visit around the holidays, you’ll find the whole house covered in festive winter decor!

The family who owns Sybill’s has been in the restaurant business for decades, so it makes sense that all of the upscale New American–style food here is fantastic! We ordered a ton of appetizers, like the fried mushrooms, scallops, and lobster bisque soup, and I’m still thinking about this meal.

1100 N. Jefferson St., St. James. Open daily 11am–9pm.

Uranus Fudge Factory

The best way to visit Uranus Fudge Factory is with no expectations, so I don’t want to ruin it too much for you. The concept was developed by entrepreneur Louie Keen, who aimed to create a unique and entertaining destination for travelers. He transformed what was previously a gas station into an eclectic shopping and entertainment area, featuring novelty stores, a fudge factory, a general store, a tattoo parlor, a bar, and other unconventional attractions.

Rows of barrels filled with every flavor of taffy imaginable, T-shirts with phrases that will make you check three times to make sure you read them right, and a slew of random objects are just a few of the things you’ll find here. Of course, you can’t miss out on grabbing some fudge too. Make sure you take time to explore the entire place!

14400 State Hwy Z, St. Robert. Open daily 8am-9pm.

If you have more time, here are some additional suggested stops for this leg of the journey:

• A Slice of Pie – A classic dessert spot just off the highway with a variety of pies. Get the apple!
• Devil’s Elbow Bridge – A historic bridge on Route 66 known for its scenic beauty and graceful arches over the Big Piney River.
• Frog Rock – A roadside oddity: a large rock painted to resemble a whimsical frog, capturing the playful essence of the highway.
• Route 66 Museum – Showcases the rich history and cultural significance of the iconic highway through exhibits and artifacts.
• Boswell Route 66 Park – A serene park paying homage to Route 66, offering a peaceful retreat and a glimpse into the road’s legacy.
• Redmon’s Candy Factory – A delightful confectionery crafting handmade candies, embodying traditional sweet-making techniques.
• Conway Welcome Center – An inviting stop offering traveler amenities and information, welcoming visitors to the area with warmth and assistance.
• Hubble Space Telescope Replica – A scale model offering insight into the wonders of space exploration and the groundbreaking Hubble Space Telescope’s contributions to science and discovery.

Accommodation: Rail Haven Motel
If you’re looking for a place to stay in Springfield, the Historic Best Western Rail Haven is your spot! You’ll find quaint rooms with everything you need and easy access to downtown Springfield, just a five-minute drive away. Plus you’re only a few minutes from Cherry Street, a hotspot for young professionals to shop in the various boutiques and enjoy drinks and food at the Royal and Tie & Timber Beer Co.

Missouri Route 66 Road Trip Itinerary: Day 3

Druff’s Diner
If you can’t tell yet, Missouri does breakfast incredibly well, and I loved each spot we went to. You’ll find Druff’s in the colorful streets of downtown Springfield. If you need more coffee before you head out to explore, I really loved Mudhouse Coffee right down the street, too!

331 Park Central E., Ste. 101, Springfield. Open daily 8am–4pm.

Route 66 Car Museum

When I was younger, I wanted to be a car designer. So for me, visiting this museum was so cool, because it showcases over 70 vintage sports and movie cars, and celebrity vehicles ranging from the early 1900s to more contemporary models. I was very tempted to take the old Bronco home with me (not that I could have… but she was just so cute!) You’ll also find an extensive flea market full of unique finds in the back corner of this museum that’s worth checking out.

1634 W. College St., Springfield. Open daily 9am–5pm.

Finley Farms

Located on the banks of the Finley River, Finley Farms is a sprawling gathering place made up of the Ozark Mill property and featuring farm-forward restaurants, vibrant event venues, a riverside wedding chapel, and an urban farm. The farm-to-table menu was amazing — I ordered the salmon grain bowl and chicken dumplings — and the setting was even better. If anyone is getting married in Missouri, I highly recommend checking out this place as a venue!

802 Finley Farms Ln., Ozark. Open daily 11am–9pm.

History Museum on the Square
In this museum you’ll journey through eight interactive galleries to see how Springfield and the region shaped American history. There are also various permanent and temporary exhibits worth checking out, including exhibitions on Native Americans and the Civil War. There’s also a cool exhibit on a shootout with Wild Bill Hickock that happened right here in Springfield, which is considered the first shootout of the Old West.

154 Park Central Square, Springfield. Open daily 1pm–5pm. Admission is $16 ($13 for seniors, $10 for kids).

Cruising down Route 66 in Missouri was like diving into a time capsule filled with all things awesome about America. Every twist and turn had its own story to tell. Quirky towns with retro diners and flashy signs made me feel like I was living in a classic movie, and the beautiful landscapes and natural wonders left me in awe of what this state truly has to offer. Trips like this remind me that we don’t always have to travel far from home to experience a whole new world!

I think Missouri is a highly underrated state, and this three-day road trip down Route 66 will show you why. If you’re planning to explore more of the United States next year like I am, I promise you Missouri is worth a visit.

Raimee Iacofano of RaimeeTravels is a travel content creator with over 10 years of world travel experience. She lives on finding cheap flights, fantasy novels, and all things film. Hailing from Detroit, Michigan, she now calls Los Angeles home and uses her platform to simplify travel planning, share unique travel hacks, and offer invaluable tips to help her audience navigate the globe with savvy and ease.