With her unfaltering dedication to fight against patriarchal convictions in Victorian Britain, Augusta Webster (1837-1894) is featured as a groundbreaking activist poet who grapples steadfastly with the problems of gender discrimination and dualistic constructions of womanhood. At the center of Webster’s feminist agenda are Victorian women’s educational and suffrage rights, equal employment opportunities and economic freedom. Webster’s reformist character is profoundly manifested in her choice of nonconformist, radical female characters as the spokesperson of her ideas, who are condemned and marginalized by the Victorian society. The main concentration of this study, hence, is to analyze these maverick female characters in “Medea in Athens”, “A Castaway”, and “Sister Annuciata” to unravel Webster’s political, activist impetus to destabilize dichotomous conceptualizations of womanhood, either as the angel in the house or the fallen woman in Victorian society.