Abstract: This article explores the childrearing practices of New England ministerial families in the late seventeenth century. The article argues that Puritan literary practices ensured a certain degree of uniformity in relations between parents and their children, whether they occurred in a denser town setting like Boston or in borderland communities like Deerfield. The study of childhood is challenging due to the lack of self-referential sources produced by children, so attention is given to prominent diarists who raised children at this time, like Samuel Sewall and Cotton Mather, to reconstruct the parenting of young children. The article seeks also to contextualize the childhood experiences of Stephen Williams, who later achieved a degree of fame as the “boy captive” during the 1704 attack on Deerfield, as part of a larger project on his life.