In this treatise an attempt is made to emphasize the early ancestors of the Winfrey Families and the ones especially of Cumberland County, Russell County, and Adair County.
The first immigrant ancestor to America has not been determined but we begin to find positive records on the family in the Virginia records commencing with William Winfree in 1636. This was soon after the first settlement in Virginia at Jamestown in 1607. William Winfrey in 1651 and Henry Winfrey in 1676 were living in New Kent County, Virginia in 1688 and perhaps earlier. A William Winfrey who lived in Chesterfield Co., Virginia could have been a fourth brother as he was related. A John Winfrey and wife, Sarah, came from England and left a will in 1697, Norfolk Co., Va. Two Johns, two Jacobs, and two Charles Winfreys had children but to whom each belonged has not been determined. Sixteen Winfree - Winfrey men served in the War for Independence from the colony of Virginia. The Winfreys migrated from Virginia to the Carolinas and other Southern States as well as westward into Kentucky and Tennessee. Our John Winfrey, born Aug. 17, 1728 lived in Powhattan Co., Va., where two of their sons were born; namely, Philip in 1764 and Henry in 1767. This part of Virginia is only about 60 miles from where George Washington lived in 1732. The family moved to Buckingham Co., Va., about 1775 and were living there when Philip Winfrey entered the war and were still living there when Philip was discharged in 1781. In the 1790’s John Winfrey and three sons, Philip, John, and Henry, moved 600 miles west to the Green River area in what was then Lincoln County, Ky.
A note here concerning Ky. counties is helpful in determining where records of the times may be located. First Virginia claimed the Kentucky area as part of her Augusta County before white men had explored the area. It was included in her Virginia County of 1684 (?). Dr. Thomas Walker explored the eastern area as early as 1750. Daniel Boone, born in Pa., of English parents, moved his family into Ky., area from Rowan Co., N. Car. on the Yadkin River in 1773, but he had explored the Kentucky area in 1764. In 1750 Col. Richard Henderson organized the Transylvania Company. He was from North Carolina. He purchased from the Indians almost half of what is now the state of Kentucky, a1l the land between the Kentucky River in the Central part of the state and the Cumberland River in the extreme western part of the state. In 1774 Harrodsburg became the first permanent settlement in Ky. In 1775 Boonsesboro was founded by Daniel Boone. Previous to these explorations all of Kentucky had been made part of Fincastle Co., Virginia. During Boone’s activities in the section, Kentucky was designated as Kentucky Co., Va., in December 1776. In 1780 it was divided into three counties, Lafayette, Jefferson and Lincoln. In 1790 those three counties were subdivided into nine counties, Mason, Bourbon, Woodford, Fayette, Madison, Jefferson, Mercer, Nelson, and Lincoln. Lincoln county has records from 1792. In 1792 Green county was formed from Lincoln and Nelson counties. In 1798 Cumberland Co. was formed from Green Co. In 1801 Adair Co. was formed from Green Co. In 1825 Russell Co. was formed from Cumberland, Adair, Wayne and Pulaski Counties. In 1842 Clinton County was formed in 1842 from Wayne and Cumberland Counties.
The John Winfrey and three sons mentioned above moved to the area then called Lincoln Co., and later Green Co., on the Green River near the present Dunnville area of Adair Co., and formerly was a part of Lincoln County of 1790. Undoubtedly they traveled the wilderness road thru the Cumberland Gap. When Philip Winfrey took his 100 acre grant on May 13, 1799 (certificate of Settlement No.1253) this part of Lincoln Co., had become part of Green Co., and in 1801 part of Adair County. John Winfrey (Winphrey) the father received U. S. land Office Military Warrant No. 1684 for 100 acres of land in the same area, but we have no record of his settling on his grant. He presumably, as did many others, disposed of it by sale to another. There were no Winfreys on the Tax Rolls of 1790 but in 1800, John and three of his sons, Philip, Henry and John are shown.
Another son of John Winfrey was Israel S. Winfrey who moved from Culpepper Co., V., in 1804 to Kentucky. In 1807 he bought 270 acres on the Cumberland River from a land owner or Adair Co. and paid $14.50 for the nearly level land in the upper end of Rock House Bottom Community then a part of Cumberland Co., but which became a part of Russell Co. when it was formed in 1825. The deed is recorded in the Clerk’s office of Cumberland Co., Burkesville, Ky. Rock House Bottom is named after the famous natural bridge like passageway thru the rock cliff from Cumberland River to a creek and thru which a portion of Cumberland River flows at high tide of some 20 or 30 feet and reenters the main stream of Cumberland River at Winfrey’s Ferry about one mile from the “Roc House”, but the main stream flows around Rock House Bottom about 7 miles. The passage thru the cliff is probably 100 feet wide, 30 feet high, and 150 feet thru to the creek.
