Route 66 Part Two

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Continue your Route 66 Trip. Starting from Cuba, Mo., start your great American road trip by heading west on Route 66 to see everything from picturesque courthouses to re-creations of Old Route 66 filling stations. Explore the Route 66 museum, quaint bed and breakfasts, wineries and more as you make one of the great American road trips down Route 66 in Missouri.


A. St. James Winery

Is it ever too early to sip wine? We won't judge, and your friends at St. James Winery won't, either. Hey, they've got juice, too, so enjoy the free, self-serve tasting bar. There are 32 varieties of wine and juice. Wine cellar tours are offered hourly on Saturday and Sunday; other days by reservation.

B. Stonehenge Replica

This half-scale replica of Stonehenge was created using water-jet technology at Missouri University of Science and Technology.

C. Wooden Railroad Trestle Bridge

Built in 1941 to bring building supplies to Fort Leonard Wood. Stop at the scenic overlook from Teardrop Road, and then continue east to Trophy Lane and turn left to the old trestle bridge and journey back in time to see why Route 66 has become one of the great American road trips.

D. Route 66 Shield – Waynesville

Great photo opportunity on the square in Waynesville!  Gather 'round this 8 foot x 8 foot Route 66 Shield for the perfect selfie or group photo.  


A. Route 66 Museum

Take a self-guided tour of this museum, which features recreations of a 1950s gas station and a classic diner, along with displays of antique cars, a collection of Route 66 books, magazines and videos. It’s the perfect place to add a history lesson to your Route 66 trip.

B. Dowd’s Catfish and BBQ

Dowd's Catfish and BBQ offers award-winning Southern fried catfish, barbecue, steaks, seafood, burgers, sandwiches, and salads.

C. Gary’s Gay Parita

This recreation of a 1930 Sinclair gas station takes you for a journey in time. The site includes a replica station, along with original pumps and other memorabilia from the heyday of Route 66.

D. Jordan Valley Park

Route 66 was born in Springfield (it was here where the highway officially was named) and today, a section of the highway borders Jordan Valley Park. Take a break from driving and stretch your legs, while enjoying open spaces and water features; any kiddos in your group will enjoy the playgrounds.


A. Jasper County Courthouse

Enjoy an evening stroll, and wonderful photo opportunities, around this magnificent courthouse. Built in 1894-95, this Romanesque Revival building is constructed of Carthage stone and listed on the National Register of Historic Places. The Jasper County Courthouse is said to be the second-most-photographed building in the state of Missouri.

B. Grand Falls

It's a little bit off the Route 66 path, but a trip to Grand Falls, on Shoal Creek, is worth the trek. One of Missouri's most scenic destinations, it's the largest, continuously flowing natural waterfall in Missouri, plunging 25 feet.