A large subset of Mary Wilkins Freeman’s short fiction revolves around the tension generated by the protagonist’s obstinacy and resistance to peer pressure, often in relation to deceptively trivial matters. Regionalist readings of her work have long established the relationship between this motif and the typical “New England will,” shaped by centuries of Puritan discipline and emphasis on individual conscience. Yet, far from reifying discourses on national identity, I argue, Freeman’s sketches exploit regionalism’s cultural marginality to challenge the dominant ideologies of the time, in particular those of separate spheres and eugenics. By featuring characters that depart from normative subject categories and endowing them with a strong sense of ethics and determination, the stories offer powerful examples (and, in some cases, counter-examples) of individuals struggling to assert their individuality and negotiate some form of agency within the rigid ideological constraints of the time. Drawing on a Foucauldian understanding of regionalism as a discourse rather than a literary category, this paper focuses on Freeman’s subversion of gender norms in particular, and traces its textual manifestation in a large sample of her early short fiction, including but not restricted to "An Independent Thinker" (1887), "A Balsam Fir" (1901), "A Patient Waiter" (1886), "The Parrot" (1900), "An Honest Soul" (1884), "A Church Mouse" (1889), "Louisa" (1890), and "The Revolt of Mother" (1890).