Frank Winfield Woolworth New York, to John Hubbell Woolworth (1821–1907) and Fanny Woolworth (née McBrier; 1832–1878), and had a brother, entrepreneur Charles Sumner Woolworth (1856–1947). His parents, John and Fanny Woolworth, were devout Methodists and sympathetic to the Northern side during the Civil War – they raised their two sons, Frank Winfield and Charles Sumner, accordingly. At the age of four, Woolworth told his parents that one day he would become one of the peddlers that sometimes came calling; he and Charles would play "store"; Frank would set up merchandise to be sold to his brother. As was common at the time, Woolworth
Frank Winfield Woolworth finished his schooling at the age of sixteen, yet with only basic knowledge and no experience he was unfit to begin working in any legitimate store. Undeterred, he applied to many shops in the area, every time receiving a resounding "No." Woolworth attended a business college for two terms in Watertown, New York, after having received a loan from his mother. In 1873, Woolworth worked as a stock boy in a general store called Augsbury & Moore's Drygoods in Watertown. His first experiences at Augsbury & Moore's would serve as the starting point to his own business venture and innovations.