Trip 16 · Madison, Indiana (border run)
Hoosier Waterfalls & Trains on Main
TrailsOdditiesborder runLittle kids OKGrade-school sweet spotTeens won't groan
Cross a bridge that hums under your tires, crest a hill to the book's best river reveal, hike a canyon with four named waterfalls, and stand (well back) while a freight train splits a shopping district.
The route
Old Frankfort Pike → Frankfort → US 421 north through New Castle and Bedford → Milton → Madison, IN → optional IN 56 to Vevay → US 42 through Carrollton → home
Stops
Frankfort warm-up
Cross the Singing Bridge (its steel deck hums a note under your tires), salute Daniel Boone's cliff-top grave, and pocket bourbon balls from Rebecca Ruth, where the candy was invented.
The Milton Hill
US 421 crests and drops to the Ohio with Madison's church spires across the water — one of the great river reveals. First gear, jaws open.
Clifty Falls State Park
Four named waterfalls, a boulder canyon, and an abandoned railroad tunnel (flashlights, when open). Spring flow, fall color.
Madison
A hundred-plus blocks of preserved 19th-century river town: mansion lawns, the cast-iron Broadway Fountain, soda-fountain candy shops.
La Grange trains
Detour either direction: full freight trains run straight down the middle of Main Street several times a day. Stand behind the lines; cover the milkshakes.
File a field report
Found a new dairy bar? Bridge out? Dog mayor re-elected? Email a field report and the best dispatches get published (first names only) on the Field Notes page.