Source: Zach, Karen Bazzani. Montgomery Medicine Men ... Crawfordsville: MCHS, 2002 - note addition / correction to the original - figured if I wrote it I can make the changes - lol - kbz
Always giving a "pleasant" greeting, Dr. Winston could be found making his rounds, on one of his three fine horses, while gnawing on a let of mutton. He was tall and rode at a gallop, erect in his saddle. He was noted to be "as agile as a cat." Born in Richmond, Virginia in 1792, it is said that he inherited slaves and immediately set them free, (although coming from a Quaker family who didn't believe in slavery, I - kbz find that questionable). Having been born and raised a Quaker, he was the son of George and Judith Winston. He was a close friend to Major Whitlock and knew both President Madison and Monroe.
His wife was Elizabeth Cheadle Clark, whom he married in Virginia. The Winstons came to Montgomery County, entering land on New Year's Day, 1830. They are found with a family of five, livingi n Franklin Township, Sec 17, in the 1830 census. Among their children were: Ambrose; Charles; William; Bowling and Pleasant, Jr. All but the last two returned with their mother to Virginia about 1855 but must have returned as at least Pleasant and Elizabeth are found in the 1860 and 1870 Franklin Township census.
Pleasant is buried in the Farmers Institute Cemetery in Romney, Indiana dates are: 29 July 1792 - 13 January 1876. with his beloved wife, 25 Sept 1800 - 4 Nov 1852 but she is buried in Altavista where some of her sons are buried (Campbell Co Virginia). Note that her father was Bowling Clark and mother Elizabeth thus Bowling their son. Pleasant's sister, Eliza married Dr. J.G. McMechan of Drlington. WInston's medical training was received at Jefferson Medical College in Philadelphia.
** Above Ambrose was named Ambrose Whitlock Winston after his father's dear friend and that name continued for several generations, with at least Ambrose (and wife Lela Rucker) daughter, Elizabeth who married John William Clay and had Ambrose Whitlock Clay. Ambrose Winston served as 2nd Lt. in Company E, Virginia 58th Infantry. He is buried in the Winston - Clark Cemetery in Altavista, Virginia. (30 May 1835 - 11 May 1897) - son Bowling Henry Winston is also buried there (25 July 1822 - 30 April 1892).
** Pleasant and Elizabeth married in Campbell County, Virginia 22 December 1820.