Until recently, Wallace Stevens’s oeuvre has gone largely neglected in studies of urbanism in literary modernism, as his verse mostly neglects the sweeping skylines often found in the poetry of more pronouncedly urban modernists. However, as seen in recent scholarship and as Daniel’s chapter demonstrates, Stevens was profoundly influenced by modern urbanization during his formative years in New York City and often turns to understated cityscapes as fit environments for his ongoing exploration of the right aesthetic relationship between reality and imagination. This chapter offers a brief study of Stevens’s urbanization of mind before providing a close reading of two major modes of urbanization throughout his works: a “dark,” antipoetic urbanization in which city architectures prevent contact with nature and community, thereby also preventing the creation of vibrant poetry, and an organic, aesthetic urbanization where cities are sites of poetic inspiration and surprising connection with the more-than-human world. Rather than resolving this tension, Daniel proposes that Stevens’s vacillation between these two modes is itself characteristic of the multiform and often ambivalent ways the poet engaged with modern urbanism.