After graduating from The Academy at Belleville, NY, Oscar taught school for one year. He then engaged in the mercantile business in Mannsville, NY, under the firm name of O. Sheffield & Co. He continued in this business for four years, during which time he also served as Village Postmaster. Around 1849 he switched careers and went into the business of sheep handling. When Oscar and his wife Adeline moved to Wisconsin, he became a farmer and also taught instrumental and vocal music for a number of years.
In the 1880 Federal Census, Oscar & Adeline are living at Spring Prairie (District 234), Walworth Co., WI. They are near John & Martha Middleton, Oscar's sister and brother-in-law, and their mother Hannah (Smith) Sheffield who is living with the Middletons. A Hattie Sheffield age 17 is a servant in the household of Frank & Hattie Palmer and their baby girl Mabel. I am making an assumption that Hattie Sheffield is a daughter of Oscar & Adeline. County records confirm that they did have a daughter Harriet, known as Hattie.
According to the Walworth County Historical Society, Oscar Smith Sheffield came to Troy, Walworth County, in 1856; his obituary says he came in 1855. The family moved to Spring Prairie in 1860, and to Elkhorn in 1884. It is also noted that he lived at Lafayette.
Oscar was nearly 92 when he died. Even in his old age he was known to be an avid reader, and kept well informed on current events. (source: obituary in The Elkhorn Independent of Walworth County, Wisconsin)