^Looking west where Indiana 66 enters New Harmony, February 2023.
Indiana State Route 66 runs in southernmost Indiana, through Evansville and near the Ohio River for much of its length. It begins in New Harmony, at the eastern approach of a now-closed bridge that once carried Illinois 14 over the Wabash River. From New Harmony, Indiana Route 66 heads east into Evansville, switching places with Indiana Route 62 to take its place as the southernmost east-west Indiana highway, near the Ohio River. East of Cannelton, Indiana Route 66 and the Ohio River both take a more northerly turn, and even after the Ohio River turns easterly again, Indiana Route 66 proceeds to zigzag northeasterly before ending at US Route 150 in Hardinsburg.
My photo for Indiana Route 66 is the sign assembly facing south at the south end of Indiana Route 261 in Newburgh. Note that this photo faces south as Indiana 261 begins to the north, so this sign assembly is seen by drivers on a road that is not a marked state highway. This photo was taken in April 2018.