Missouri Route 66 Road Trip Itinerary: Day 1

Start your adventure at the National Museum of Transportation in St. Louis. This museum showcases an impressive collection of planes, trains, cars, and trolleys. One highlight is the futuristic Virgin Hyperloop, designed to move cargo at lightning speeds using magnetic systems in a vacuum tube. While it may never come to life for passenger use, it’s a fascinating look at the future of transport.

Next, explore the stunning Meramec Caverns, the largest cave system in Missouri. On a 45-minute guided tour, you’ll witness millions of years of geological formations, complete with a colorful light show. It’s a family-friendly stop you won’t want to miss.

For lunch or dinner, stop by Missouri Hick Bar-B-Que in Cuba. This cozy log cabin-style restaurant is known for its mouthwatering mac ‘n’ cheese, pulled pork, and ribs. Grab the sampler platter to taste it all!

Additional food stops:

  • Hi-Pointe Drive-In for burgers and sweet potato tots.
  • Ted Drewes Frozen Custard for their famous “concrete” custard.
  • Big Chief Roadhouse for a historic Route 66 dining experience.

End your day at the Wagon Wheel Motel in Cuba, an iconic spot with 1930s charm updated for modern comfort. You can’t miss its neon sign lighting up your way to a good night’s rest.


Missouri Route 66 Road Trip Itinerary: Day 2

Kick off Day 2 with breakfast at Shelly’s Route 66 Café, where you’ll get diner-style vibes and amazing biscuits and gravy. Their coffee is a local favorite!

Next, swing by Fanning 66 Outpost, home to the world’s largest rocking chair. At 42 feet tall, it’s a quirky photo op and a fun place to grab snacks for the road. Don’t forget to say hi to their adorable orange tabby cat!

Head over to St. James Winery, Missouri’s largest award-winning wine producer. Enjoy a free tasting and take in the festive atmosphere, especially during the holidays.

For dinner, treat yourself to an elegant meal at Sybill’s Restaurant in St. James. This family-friendly spot serves upscale New American cuisine in a beautiful manor setting. Their fried mushrooms, scallops, and lobster bisque are worth every bite.

Wrap up your day with a stop at Uranus Fudge Factory in St. Robert. It’s a whimsical, quirky destination filled with novelty shops, a fudge factory, and more. The perfect spot for some sweet souvenirs!


Missouri Route 66 Road Trip Itinerary: Day 3

Start your morning with breakfast at Druff’s Diner in Springfield, a colorful downtown gem known for great coffee and even better breakfast.

Next, visit the Route 66 Car Museum to explore over 70 vintage and movie cars, including celebrity vehicles. Don’t miss the flea market inside, where you can find unique treasures.

For lunch, stop by Finley Farms, a beautiful riverside spot serving farm-to-table dishes like salmon grain bowls and chicken dumplings. It’s also a lovely wedding venue if you’re planning a special event!

Finally, visit the History Museum on the Square, where you can dive into interactive exhibits on Springfield’s role in American history, including the Wild Bill Hickock shootout, considered the first Old West duel.

In Summary:
Driving along Route 66 in Missouri is like stepping back in time. Every small town, roadside diner, and quirky attraction tells a story of Americana. The breathtaking landscapes and unique stops along the way make it a road trip to remember!

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