The highway, its promise of freedom and mobility, stands as a source of intrigue in American culture. Yet, the asphalt and dashed lines that cut across the country conceal the contentious history that accompanied interstate highway construction. This dissertation examines the social and spatial meanings of interstate highway plans in the United States at different historical and geographic scales. This account begins in the late 1930's and travels through the mid 1940's where I discuss Norman Bel Geddes's 1939 Worlds Fair Exhibit, "Futurama" and Robert Moses's 1944 Baltimore Arterial Report. This analysis demonstrates how each man inscribed social values into proposed developments within geographic space. From here I move to Baltimore where from 1944 until about 1979, countless proposals called for the construction of an arterial highway that would cut into the heart of the city. By drawing from the archival records left by Movement Against Destruction (MAD), Relocation Action Movement (RAM), and other groups in that fought against roadway plans in Baltimore, I explore how activists lived, understood, and challenged the new social arrangements embedded in the proposed highway system. I introduce the term infrastructural imaginaries to account for how the proposal or construction of spatially embedded systems seeks to transform lived material and geographic arrangements. The concept of infrastructural imaginaries expands upon Sheila Jasanoff and San-Hyun Kim's "sociotechnical imaginaries" to address how proposed futures appropriate spatial environments and how people lived, understood, and conceptualize themselves within these emergent spaces. The framework of infrastructural imaginaries utilizes Henri Lefebvre's conceptual triad of spatial practice, representations of space, and representational space to analyze the dynamic interactions between infrastructure planning, lived experience, and articulations of possible futures. To study the infrastructural imaginary, the immaterial form, provides a fertile space from which to isolate places where systems fail to take hold, where alternative understanding emerge, and where new forms social interaction takes place. / Ph. D. / The interstate highway, its promise of freedom and mobility, stands as a source of intrigue in American culture. Yet, the asphalt and dashed lines that cut across the country conceal the contentious history that accompanied interstate highway construction. Following the passage of the 1956 Federal Aid Interstate Highway Act movements called ‘freeway revolts’ began in cities across the United States. These protests resisted the construction of highways in urban areas. Additionally, these social movements called attention to the planning practices that condemned the houses of low income and minority populations, clear-cut park land, and disrupted the urban fabric. This dissertation examines Baltimore’s ‘freeway revolt’ using archival documents left by the many activist groups who participated in attempting to stop the highway. Rather than presenting a comprehensive history of these events, this dissertation pays attention to how social understandings of geographic space contributed to highway plans, organized activism, and the practices of those who lived under the threat of impending infrastructure.