It makes sense that many women have sought out utopias. Oppressive and restrictive social systems drive those excluded to claim "there must be something better than this." While many women have engaged in utopian flights of fancy, fewer have had the opportunity to bring their vision into being. Jane Addams and Dorothy Day are two women who imagined the possibility of a different world and each initiated influential movements to make their dreams a reality. Both created communities devoted to social service, worked among the oppressed, had radical ideas about social morality, and both were staunch pacifists. These two pioneering women also represent a stark contrast in utopian thinking. One was a pragmatist feminist who fought for women's suffrage becoming a political force to be reckoned with. The other was a Catholic anarchist who eschewed the right to vote and refused to participate in politics. This article seeks to bring attention to the intriguing continuities and discontinuities of the activist philosophies of Jane Addams and Dorothy Day. While both utopian visions have their appeal, I suggest that ultimately Day's approach is one of charity and Addams's is one of education, and that the latter holds the most promise for feminist activist theorizing.