Jan/Feb '26

Missouri Route 66

6 min read

A lot of Route 66 has been consumed by the interstate, but we tried to stay on the old route, like this Missouri segment, as much as possible.

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After crossing the Mississippi from Illinois, Route 66 winds through more than 300 miles of rolling hills, cozy towns, and vibrant green countryside of Missouri. The Show Me State features some of the longest rideable stretches of the original highway still in existence today.

Riders on Missouri’s portion of Route 66 will encounter a variety of attractions that are uniquely Missourian. St. Louis is an urban gateway, while towns like Rolla, Lebanon, and Springfield showcase preserved motels, diners, murals, and vintage gas stations. Landmarks such as the Chain of Rocks Bridge in St. Louis, the Wagon Wheel Motel in Cuba, and Meramec Caverns in Sullivan are some of the most popular stops.

This used to be the biggest rocking chair in the world, until the town of Casey, IL, went and built a bigger one. Now this chair in Fanning, MO, is the second largest.

Riding Missouri’s Route 66 is best done over two to three days. Many original road alignments remain intact, particularly through rural areas, so taking the time to follow these stretches provides an authentic Route 66 experience.

Missouri’s Official Mural City—Cuba

Cuba proudly wears the title of Mural City, a fitting distinction for the town of just over 3,000 residents. Situated about 85 miles southwest of St. Louis in Crawford County, Cuba has long served as a pit stop for travelers—originally for trains, and later for cars and motorcycles traveling the Mother Road.

The town was platted in 1857, shortly before the St. Louis-San Francisco Railway arrived, and grew as a rest stop for the surrounding farming community. Its name likely comes from two ex-gold miners commemorating a vacation to the Caribbean island, although some suggest it reflects U.S. foreign politics of the 1850s.