This article outlines expressions of female masculinity in writing from rural New England. An initial framing of the enclosed New England garden as symbolic of feminine normalization allows for an analysis of two forms of subversion of this norm in regional short stories from the nineteenth century. The article begins with an exploration of the figure of the female farmer (and the resulting rejection of the traditional True Woman) in short stories by Mary E. Wilkins Freeman and Sarah Orne Jewett. It continues with a comparison to newly emerging depictions of the masculine New Woman symbolically situated in the open expanse of the Midwest, as found in Willa Cather's short story "Tommy, the Unsentimental." Such a comparative line of questioning enables deeper reflection on regional literary expressions of female masculinity at the end of the nineteenth century.