In 1812, Kaskaskia and Shawneetown were the leading towns of Illinois. Shawneetown was a port of entry on the Ohio River for immigrants from the east and south. There was a demand for the shortest overland route from Shawneetown on the Ohio River to Kaskaskia on the Mississippi River.
In 1816, Congress granted $8,000 to have the road surveyed and cut out. The road was cut from Kaskaskia to Dements settlement, where Plumfield is now located, just west of West Frankfort in Franklin County, Illinois. The road was completed but there was no money for building bridges across the streams such as Little Muddy River, Big Muddy River, and the Saline Creeks.
This old road came from Kaskaskia to Mulkeytown with a stop at the old Silkwood Inn, across Six Mile township, across Big Muddy River to Plumfield with a stop at the "public well" to water the stock. It went on through West Frankfort, and over Frankfort Hill where the old "Franks Fort" and the first county seat was located, with a stop at the Dimmick Hotel for over night lodging where Abraham Lincoln later spent the night. Then on through Garrett's Prairie east of West Frankfort where Moses Garrett built his tavern which was the first building in the county and where they first held court. Then by way of Fitt's Hill, Jordan's Fort, Fancy Farm, Thompsonville, and on toward the south east to Shawneetown. This route was known by the early settlers as "The Shawnee Trail" and was named after the Shawnee Indians that lived in the area at that time.