The earliest settlers of Scott Co. came mainly from VA, North Carolina and Kentucky. The two main routes for these settlers were the overland route through the Cumberland Gap and over the Wilderness Road through Kentucky or down the Ohio River from Pennsylvania on flat boats.
Many, if not most of the early settlers of Scott County were "squatters".In other words they lived on the land without legal ownership. This was not unusual for most of those who came West in those days. A person could pick out his land, clear the trees, build a cabin and plant crops. When he had accumulated enough money for a down payment, he would saddle his horse,go to the United States Land Office and enter his land. The government was lenient and the land was cheap. Payments could be made over a four year period. When it was paid up, the government issued a patent, signed by the President of the United States.
According to Carl Bogardus M.D. in "The Early History of Scott County,Indiana 1820 - 1870", the first white man to attempt a settlement was James Harrod, Jr. He selected a spot about a mile east of present day Lexington and built a cabin there in 1796. However, John Kimberlin (along with sons Daniel and Isaac) who came down the Ohio on a flat boat from Green Co.,PA in 1805 is generally credited with being Scott County's first settler."Kimberlin, a Revolutionary War veteran, was the first person to purcahse land in what is now Scott County. In 1804 he bought Tract 264 of land grant to soldiers of George Rogers Clark. His family settled in 1805 in a well built cabin northwest of here, cleared land, built fences, and farmed. He and his wife are buried in the cemetery southwest of here. (The John Kimberlin Farm Historical Marker, 5765 South Westport Road, Nabb, IN)
After Pigeon Roost Massacre in September 1812, his cabin was converted to a fortified blockhouse and sheltered area settlers. Nearly 600 mounted volunteers from Kentucky and Indiana Territory came to protect the area,encamped on his land, and used his supplies. He petitioned the U.S.Congress in 1832 for payment and received $150 in 1834."
Also in 1805, Jesse Henley of North Carolina came to what became Scott Co.and built a tavern for the benefit of travelers and to use as a base for trading with the Delaware and Shawnee. His was the first land entry to be made in what is now Scott Co. His patent was dated June 20, 1809.
In 1809 a group of twelve pioneers and their families led by William E. Collings, came from Nelson Co., Kentucky and established the ill-fated Pigeon Roost settlement which was destroyed by the Shawnee in September of 1812. Collings patent, however, is not dated until 1816.
Many of the men who filed for patents in Scott Co. were veterans of the American Revolution. Most entered their land at least four years before the date of their patents so we can be fairly sure they were squatters even earlier. Approximately 900 patents for land were issued in Scott Co. between 1809 and 1820 when Scott became a county. Some of those patents were issued to the following: James Anderson, William E. Collings (1816), Matthias Mount (1816),Spencer Hougland, Moses Hougland, Jesse Henley, John Wingate, James Harrod,David Clark, Zebulon Foster, Walter Spencer, Sr., James Hougland, Isaac Estill, Willliam Harrod, John B. Pittman, John Clinkinbeard, Solomon Beach(1820),Samuel Beach (1820) Thomas Broady, Thomas Collings, Francis Snowden and William E. Collings (1820).
Note: Information from "The Early History of Scott County, Indiana 1820-1870 by Carl R. Bogardus, Sr., M.D., published by The Scott County Historical Society, 1970.