Winfrey Genealogy - Western NC

Marty and Karla Grant

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Winfrey Genealogy - Western North Carolina

Welcome to my Winfrey genealogy pages. I am interested in the Winfrey surname in Western NC. My own ancestors resided in Surry, Wilkes and Cherokee Co., NC, but I’m interested in other Winfrey families in the vicinity also.

The Winfrey surname is generally of English origin. The name can also be spelled Winfree.

Neither Winfrey nor Winfree made the Top 1000 most common surnames in the United States in 2000 or 2010.

My most recent Winfrey ancestor was my 3 times Great Grandmother Caroline C. Winfrey (1822-1916) who was born in Surry Co., NC. That’s where she married James S. Wright (1813-1902) ca 1838. They moved to Cherokee Co., NC in the 1840s where they remained the rest of their lives. She had 17 children, nine of which lived to adulthood. She is a daughter of Caleb and Arabella (Moody) Winfrey.

Caleb Winfrey (Jr) (c1800-1860s) was born in Surry Co., NC. He married there ca 1821 to Arabella Moody (c1803-aft 1880). They moved to Cherokee Co., NC in the 1840s where both died. They had six children. Caleb (Jr) is a son of Caleb and Nancy (Bowles) Winfrey.

Caleb Winfrey (1755/60-1837) was probably born in Virginia. He came to Wilkes Co., NC with his parents in the 1780s. He married Nancy Bowles (c1770-c1809) ca 1789, either in Wilkes or neighboring Surry where they moved around that same time. She died in Surry ca 1809. Caleb married again in late 1809 to Mary Hamlin (c1785-aft 1860). Caleb and Nancy had six children. He and Mary had two. Caleb is a son of Isaac and Sarah (—) Winfrey.

Isaac Winfrey (c1735-1817) may have been born in Virginia, but I don’t know for certain. There were several Isaac Winfreys in Virginia records during his lifetime, so it isn’t clear which, if any of those, was him. Our Isaac married Sarah (—) ca 1750s somewhere in Virginia. (They are not the Isaac Winfrey and wife Sarah Brown of New Kent and Cumberland Co., VA as I once mistakenly believed.) They moved to Wilkes Co., NC during the 1780s and shortly afterward into neighboring Surry Co., NC. They had six children.

I don’t know who Isaac’s parents were.

Revised: July 20, 2026

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