Captain Samuel Winkley, mariner, was the earliest Winkley ancestor to settle in New England. Previous researchers have stated that this man came from Lancashire, England, but have offered no proof. The author has found the 1660 baptism of Samuel Winkley and additional evidence to confirm that Samuel Winkley definitely came from Devon, England. In fact, the name of Winkley in Devon can be traced back as early as 1219. Part One of this work covers the Winkley family in England, 1543 to 1700, and includes information on the related Clarke and Headon families. Appendices include transcripts from parish registers and churchwardens’ accounts, as well as county and other records. Part Two of this work covers the Winkley family in New England, 1680 to 1900, for a total of eight generations. A list of unknown Winkley names is included, and appendices provide wills and probate records, and war service records. An index of Winkleys and an index of other names round out this work.