Explores rural history through the experiences of three families that dominated the American peppermint oil business from its beginning in the early nineteenth century to the early twenty-first century. The rural entrepreneurs who became Peppermint Kings acted in ways that challenge traditional historical depictions of rural people. The freethinking Ranney clan built a family business that extended from Massachusetts to western New York and Michigan during the first half of the nineteenth century. The Hotchkiss brothers entered the international market and ventured into finance and banking at a time when the United States government was reducing opportunities for regional bankers. Albert May Todd brought science to peppermint farming and distilling, and advocated progressive and socialist causes as a politician and organizer of the Municipal Ownership League of America. The Peppermint Kings’ stories not only demonstrate the remarkable agency of rural people, but offer insights into how rural Americans responded to broader social changes that have typically been viewed from a predominantly urban perspective.