Born in Chautauqua County, New York, July 17, 1830. His father, Arnold Winchester, was a farmer. His father moved with his family to Pennsylvania, and then to Ohio, while Sheldon was quite young. He spent eight years with his father in Washington County, Ohio, and at sixteen years of age, with eight dollars in his pocket, he started alone for the Far West, beyond the Mississippi. He went down the Ohio on a flat-boat, up the Mississippi as a deck passenger on a steamboat to Keokuk, and thence walked to Des Moines, now the Capital of the State, reaching there with two dollars in his pocket. That was in November, 1846. The garrison buildings and soldiers’ barracks, vacated by the military the previous spring, were all the places of shelter for the few inhabitants of Des Moines. That section of the State was thrown open that year for pre-emption, the year Iowa assumed its sovereignty. In 1847, young Winchester went to Fairfield, Jefferson County, and spent a few months in a store. He then drifted eastward and landed in the Burlington Gazette office, engaging as an apprentice. His lungs were weak, the work was hard for him, and he went to Memphis Tennessee, and there spent the summer of 1848, returning to Iowa the autumn following. In the spring of 1849, he came to Winchester, Madison County and built the first house there after the county seat was located. He sold goods there one year, went to California across the plains in 1850, and spent five years, part of the time mining, part superintending a quartz mill and a saw mill, and for some time running a drug store. Returning again to Iowa, he selected a home in Eldora, and was recognized as one of its best and most enterprising citizens. During nearly the whole of this time he has engaged in the mercantile and real estate business. Mr. Winchester was the youngest member of the Constitutional Convention of 1857, and was chosen when barely eligible to the office. He represented eleven counties, the northern part of the State being sparsely settled, particularly west of the river counties and those adjacent. In 1861, he was a candidate for the lower House of the General Assembly, and was defeated on a local issue. Ten years later he ran for State Senator, to represent Marshall and Hardin counties, but there was quarrel between the two counties. Both candidates were Republican, and Marshall County having much the larger number of voters, he again failed of election. He has always been a Republican, and has often stumped the county and other parts of the State during an exciting canvass. On the 4th of October, 1856, he was united in marriage with Mahala E. Ellsworth, of Eldora.