This trail runs from Russellville, Kentucky to Shawneetown, Illinois. The trail from Russellville was a route followed by settlers from Kentucky and other parts of the upper south to Illinois and other parts of the upper plains.
- Shawneetown was an important port on the Ohio located about 40 miles down stream from present day Evansville, Indiana.
- It served after the Revolution, as an important United States government administrative center for the Northwest Territory. Shawneetown and Washington, D.C., share the distinction of being the only towns chartered by the United States government.
- Old Shawneetown, a banking center, played a role in providing capital to build the western frontier.
Between the arrival of first settlers around 1790 and the town's incorporation in 1798, Russellville was known variously as Cook's Station, Logan Court House, Rogues’ Harbour. Settlers decided on the name Russellville to honor war hero General William Russell. It is the county seat of Logan County, one of Kentucky's original counties.