The most important primary source on Head's life is William Winstanley's biographical entry published in his "Lives of the most famous English poets" (1687) – a credible if not reliable source insofar as Winstanley could claim to have been personally acquainted with Head. According to Winstanley, Head was a minister's son, born in Ireland. His father was killed in the Irish rebellion of 1641; the incidents seem to be reflected in Head's "English Rogue", the satirical romance he published in 1665. His mother took him to England where she had relatives in Barnstaple. They later moved on to Plymouth, and to Bridport in Dorset where Head is known to have attended the town's grammar school in 1650. Head was eventually admitted to the same Oxford college his father had attended (possibly New Inn Hall, from which a John Head graduated in 1628). His financial means being insufficient Head was taken from college and bound apprentice to a "Latin bookseller" in London "attaining to a good Proficiency in the Trade", as Winstanley put it.