Despite her immense popularity in the nineteenth century, Constance Fenimore Woolson's reputation dwindled substantially in the decades which followed. While her works have been rediscovered over the past thirty years, they are often categorized as regionalist writing or, in the case of her penultimate novel, Jupiter Lights, melodrama. What many fail to consider, however, is that Woolson very much considered herself a realist author, and may have been remembered as such were it not for the influence of William Dean Howells and his peers, whose very narrow parameters for literary realism excluded Woolson, among others. Unfortunately, those parameters are still with us today, and exclude many authors whose realities do not conform to Howells’s original scope. In this thesis, I examine the biographical and historical context for Woolson’s lesser-known works, arguing that they demonstrate a type of empathetic realism which must not be ignored by current scholars of American literature.