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Many of the Winegarners were teachers at Knoles School and when it was Pleasant Ridge School. They also taught at other schools. Harry Winegarner was a very prominent person in Little River. He served as a school census taker and a executer and appraiser with John H. Powell of estates when a person died. He married Laura Knoles the niece of Martin Van Buren Knoles and the daughter of Jacob Knoles.