As a modern woman who famously crossed borders, not only geographic, but also cultural and poetic, Edna St. Vincent Millay is uniquely able to illuminate the experience of border crossing. Millay's city poetry deals with border crossings in terms of women migrating from rural environments to cities. Although Millay has come to be known as a classic new woman of the city, her poetry features a state of exile experienced by modern women living in the city. She often depicts the following exilic situation: a woman in exile in the city desperately longs to escape and return to a more natural environment, where she can be free. For instance, in “Inland” and “Exiled,” the speakers feel imprisoned and crushed by the city, and they see themselves as fundamentally different from city people, in part, because of their deep connection to nature. Although these women believe the sea or the countryside offers them freedom and a refuge from the threats of city life, Millay suggests the return to nature brings new threats and leads to destruction and death. Thus, these women exist in a perpetual state of exile, as neither city nor country offers them the possibility of freedom and the home they desire. This study aims to broaden our understanding of Millay's work through an examination of the reoccurring theme of exile in four poems that have received little critical attention: “MacDougal Street,” “Inland,” “Exiled,” and “City Trees.” Paying attention to this theme of exile opens up new possibilities for the study of Millay and enhances our understanding of modern women in the city and the broader theme of exile in modern American literature.