An anonymous author in 1837 lamented that "if the world were just" the term Old Maid, instead of a pejorative, would "be a synonyme(sp) of useful virtue." While scholars have examined the domestic and beneficent contributions of single women, this paper looks at the economic involvement of single women in their local economies through two professions. Widows were often left in charge of taverns after the deaths of their husbands, suddenly making their labor in these spaces visible. Taverns were important social spaces in the relatively isolated backcountry and, therefore, the women running them could be quite powerful within the local community. Examining several widows in this position reveals how women negotiated space for themselves within the local economy. A second group of single women are located in female schools during the latter half of the period under consideration. As educating young women became more popular among the middle and upper classes, a growing demand for female schooling created an economic opportunity for educated single women. Whether for only a short period of time before marriage, during widowhood, or throughout their lifetime, female teachers tapped into an evolving image of Southern gentility as a route to independence. An examination of both female publicans and teachers presents the chance to explore how women could simultaneously employ the gender ideals of the period while ensuring their own survival. Understanding these particular women’s lives helps expand our understanding of Southern womanhood as a whole.