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Focusing on the city of New Orleans as well as on the difference between the city and the summer resort (Grand Isle) in Kate Chopin’s The Awakening, this paper examines how the urban experience of modernity shapes Edna Pontillier’s search for subjectivity in the late 19th Century. Nicknamed “the American Paris,” 19th Century New Orleans was a major city in the South both in terms of European heritage and multicultural demographics. These attributes are vindicated in the novel’s description of the streets and shops, which spur Edna’s exploration of modernity as a flâneur, i.e. a city stroller. While rambling through the city, the protagonist not only momentarily liberates herself from the role of the mother but also more fully inhabits her selfhood. Since strolling functions as a device to map class distinctions, she also sees how geographical arrangements of the city correspond to social hierarchies. However, although she feels more liberated in the city than in Grand Isle, because she is a female city stroller (flâneuse), there is clear limitation in Edna’s mobility. Women in the 19th Century were still confined to private/domestic places, and a middle-upper class woman like Edna was not expected to be seen by herself in public spaces. Edna rejects the oppressive life of a middle-upper class woman, but her inclination to walk and her attempt to get a ‘pigeon house’ close to the Pontillers’ do not result in a successful transformation in life, which suggest how difficult it is to resist patriarchal oppression. She drowns herself at the end of the novel, but as she swims far out to the sea, she tries to break down the barrier once again in her own limited way.