The earliest Matherly that I have found is John Matherly, born abt 1790 who married in 1811 Patsy McCarty. In 1814 they were in Estill County, KY, where they had James, John Wesley, Shelby, Elizabeth and Arzela. Around 1849 Shelby and several of his siblings and their extended families moved to Davis County, Iowa.
Shelby is listed in the Davis Co, IA 1850 census as Shelvern Matherly with wife Patsy and children Robert, Silas, Armilda, George, Elizabeth and Thomas. Patsy died (I presume) and Shelby married Rebecca Waldon in 1851 and had children: Albert, Martha, Sarah Elizabeth, Armilda and William. Rebeca died between 1862-1866. Shelby died in 1866. Their 3 youngest children were adopted by Jonathon Cohagen. I don't know his realtionship to George or Rebecca.
George Matherly (son of Shelby and Patsy) married 3 times. He enlisted in the 36th Iowa Co C Infantry in 1862. He was captured in April 1864 and held in the Confederate prison in Texas until February 1865. (His uncle John Wesley Matherly died in Arkansas while serving in the 3rd Missouri Cavalry, his brother Silas served in Co B 30th Reg Infantry Iowa, all of John Wesley Matherly's sons also served in the Union Army). George died in 1916 in Missouri. His children by his 2nd wife Lucinda Lewis were:
Leolist and Delilah Elenor Gertrude. Lucinda Lewis Matherly died in 1882.
Delilah "Gertie" married her cousin John Weslie Matherly, son of Albert Matherly and Margaret Riley. Albert Matherly and George Matherly had the same father (Shelby) but different mothers, so I guess that makes Gertie and John Weslie half-cousins??
So, I've given you some information on Winifred's ancestors, but I'm not sure I helped you with your grandfather, as you say Winifred was a cousin of your father? Can you tell me who his father was?
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