We drove more than 500 miles among the hills, hollows, caves and springs of the Missouri Ozarks to research this drive, and then we figured out a shortened loop for you. The route starts off Interstate-44 in Cuba and includes a hillside winery, a Civil War battlefield and state parks with amazing natural features: pink boulders at Elephant Rocks, mountaintop views at Taum Sauk and natural wading pools at Johnson’s Shut-Ins.

Get your kicks The route includes stretches of old Route-66. Snap a kitschy photo by the hilariously huge rocking chair at the Fanning 66 Outpost in Cuba.

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The mother of all road trips: Route 66 [1]

For trip planning

Route map [2]