Missouri River Bluffs Historic Military Road

This forgotten military supply route parallels the Missouri River for 24 miles between Washington and Hermann, following limestone bluffs that overlook the same muddy water Lewis and Clark navigated in 1804. Built in the 1840s to connect Jefferson Barracks with western outposts, the road drops through Daniel Boone Cave Valley where bootleggers once hid whiskey during Prohibition. You’ll pass three historic ferry crossings where Union troops moved supplies during the Civil War, including Klondike Ferry where General Price’s Confederate raiders crossed in 1864.

Easy to moderate difficulty on gravel and dirt surfaces that can turn slippery when wet. Any high-clearance vehicle handles this route, though spring rains create muddy stretches through bottomland sections. Best traveled March through November when river access points stay passable. No permits required on this mix of county roads and conservation area tracks. What makes this trip special is the constant river views and Civil War history most people drive past on Highway 100. Pack lunch and plan stops at the old ferry landings — the Missouri River tells stories if you take time to listen.