In 1792, Captain John Dunn was appointed Constable for the territory, and the first settlers to Henderson County, Kentucky were Michael Sprinkle, John Upp, William Smith, father of William Finely Smith, John Husbands, John Haussman, Jacob Sprinkle, John Kurkendall, Eneas McCallister, and John Dunn.
Eneas McCallister and his family were detained by ice while en route from the Cumberland River Pittsburgh, Pennsylvani. At that time, there were half a dozen little log cabins on the bank, and Mr. McCallister and his family took possession of one of the cabins. No Indians were to be seen on this side of the Ohio River, yet several tribes were located on the Indiana side of the river, among whom were the Shawnees, from which “Shawneetown” derived its name. The Shawnee were known to be troublesome at times, and heartless. When some young boys, Michael and Jake Sprinkle and John Upp, armed for the purpose of hunting, crossed the river in canoes, they were surprised by a party in ambush. Two boys were captured, one shot down, the fourth boy, an expert swimmer, made his escape back to Kentucky territory. The two captives were tortured in many ways—they were made to walk forced marches, then beaten with many stripes, and finally, after having undergone a terrible journey, bare-footed and almost naked, marched into Sandusky, on Lake Erie, from after living a frightful life, escaped.
The first settlers to Henderson County, Kentucky had no expensive amusements, extravagant social pastimes, glittering extravagancies, or cultured professionals. But they were cheerful people while some were rude, untutored, and uncultured. They were the fiddler in the wild woods creating ring, tickling the souls of unblacked brogans with the inspiring harmonies of " Leather Breeches," " Molly Put the Kettle On," or " Buffalo Gals." They had come a far distance to settle in a thicky woody terrain. After the cabins were built, they celebrated by dancing on a puncheon floor, splintery and unadzed, and placed their earthern or wooden tableware on a log table.
The woods, barrens and the water courses were theirs, and wild game was in gun shot of their cabin doors. The young Commonwealth had opened up the lands for settlers who began transforming an uninhabited wilderness to green fields of growing grain, and substituting the wolves for herds of cattle and sheep. In August of 1799, a meeting for the county court was held in an old log school house. built the first courthouse for Henderson County, and transformed trails into public roads.
From the Minutes of the Court we have the following order:
"Ordered, that Samuel Hopkins, Jacob Barnett and Thomas Willingham, or any two of them, mark and lay off" a road from the Public Square, in the Town of Henderson, to Smith's Ferry, on Green River, and Samuel Hopkins is appointed surveyor of that road from the Town of Henderson to the main fork of Lick Creek, and Thomas Willingham, from the main fork of Lick Creek to the ferry; and it is further ordered, that the said Samuel Hopkins, with his own hands ; Arend Rutgers, with his hands; Jacob Barnett, with his hands; Russell Hewett, with his hands; Joshua Fleehart, Thomas Smith and Robert Baird, open the said road and keep it in repair from the public square in Henderson to the main fork of Lick Creek, and that John Kilgore, Thomas Freels, John Knight Nerod Franceway, Elijah Griffith, Lawrence Rawlasson, Jr., William Rawlasson, Isaac Knight, Nathan Young. Jacob Vankird, Michael Hog, Adam Hay, Alt^ McGlaughlin, Thomas Stoll, Charles Davis and his male laboring tithables, Adam Lawrence, Jr., John Lawrence, Isaac Lusade and Jesse Kimbell, upou the said road and keep it in repair from the main fork of Lick Creek, to Smith's Ferry." This was the first road established in Henderson County. It ran to a point two miles beyond Hebardsville, where it bore to the right, and approached Green River at a point about one, or one and a half miles above the present Henderson and Owensboro Ferry. This was the crossing place for many years, but subsequently changed to Calhoun Ferry, the now crossing place.”
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Source: History of Henderson County Kentucky by E. L. Starling.