Some scholars argue that different modes of mobility produce different ways of knowing the world. Automobiles and their associated physical and social constructs are accused by some of alienating their drivers and those outside the car, whereas others see the human-machine hybrids they create as inherently connecting. Bicycling and walking are often seen as providing a more connected experience of places traversed, though the “automobilization” of these environments may conversely alienate cyclists and pedestrians through a host of social and environmental injustices, both local and global. Little empirical research has attended to this debate. This dissertation research is founded upon an epistemological position that sees knowledge (or knowing) as developed through sensual interactions with human and non-human environments and held within the body sometimes beyond words. Applying this perspective to the transportation debate evokes the guiding research question: how do the transportation practices of driving, bicycling, and walking differ in the way they shape an individual’s understanding of their local environments and mobility? This grounded theory research draws on in-depth interviews with, and commute narrative recordings and GPS logs of forty-six drivers, cyclists, and pedestrians commuting in the City of Vancouver. Thematic foci include commuters’ relationship to energy use over urban landscapes, the social and economic value of active transportation labour, and the social alienation, connection, and empathy associated with different modal hybrids. All three papers find different types and degrees of alienation associated with different transportation technologies. In general, increasing degrees of technological mediation may increase alienation, though the nuanced particulars complicate sweeping generalizations. With respect to the three modes explored here, automobility appears to alienate more than do cycling or walking. This research contributes new insights to mobilities, environmental epistemology, technology and society, environmental justice, and transportation and urban planning and policy