Best known as a New England local color writer, Mary Wilkins Freeman has rarely been associated with New Woman fiction except in passing although her sharp portrayals of complex female characters have received substantial attention. In Freeman’s early short fiction, women often function as resolute and rebellious plot-driving forces whose values implicitly align them with late nineteenth-century “New Woman” discourse. A highly mobile and versatile signifier, the New Woman took on many guises in contemporary British and American periodicals and novels and was recuperated by radical feminists and conservatives alike, resulting in multiple representations that each conveyed different feminist or anti-feminist rhetorics. A number of Freeman’s most famous characters may be read as responding to or embodying this fundamentally protean figure: Louisa Ellis in “A New England Nun” (1887), Louisa Britton in “Louisa” (1890), Sarah Penn in “The Revolt of Mother” (1890) or Jane Strong in “The Selfishness of Amelia Lamkin” (1908), to name but a few. These readings shed some much-needed light on Freeman’s ambivalent attitude towards late nineteenth-century feminisms and substantially nuance the once prevailing opinion among scholars and Freeman’s own contemporaries that her work exhibits an outdated “type of decadent Puritanism” remote from the “richer, fuller natures, stirred and swayed by intense passions” considered characteristic of the fin de siècle (Wardwell 1898). On the contrary, I argue, Freeman’s fiction displays great sensitivity towards its discursive context and engages with it in subtle and provoking ways. Far from being geographically or culturally detached from the kind of British “urban” middle-class issues traditionally associated with the New Woman (such as access to higher education, property rights, the sexual double standard, and social injunctions to marriage and motherhood) her fiction reworks and adapts these motifs to her regional locale. Drawing on a cluster of transnational discourses on the Woman Question, Freeman develops her own versions of the multitude of female archetypes that peopled Victorian imagination: neither “True Women,” “Domestic Angels,” or “Revolting Daughters,” these heroines challenge and depart from pre-determined social scripts, thereby illustrating the subversive function (if not the literary type) of the New Woman.