Check out Historic Route 66 Byway from St Louis
, MO to Joplin
, around 300 miles. You'll drive through small towns like Cuba, Rolla, Lebanon, Springfield, Carthage, and Brooklyn Heights.
Also check out Crowley's Ridge Parkway National Scenic Byway, a 198-mile drive from Malden
(at the Missouri/Arkansas border) to Helena
. You can see the maps and directions on the Federal Highway Administration site