In Baltimore, Maryland, and a select few northeastern cities, the residents of small, narrow streets enjoy an urban environment closely resembling the beloved historic city centers of Europe. However, the lower-class origins of these streets have, through much of their history, put them largely out of view for both historic preservationists and participants in the middle-class housing market. This paper examines the evolution of one block of an alley street in the Upper Fells Point neighborhood of Baltimore. It explores the bulk of the block’s history as a working class community, defined by waves of immigrants, and reveals how gentrification has changed the block in both physical form and demographic composition. The project ties the past and present together, arguing for a collection of social and psychological benefits enjoyed by residents living in a compact, nearly car-free urban environment that is quite unique for a North American city. It connects Baltimoreans from the past and present who have experienced very different social and economic circumstances but have held in common a personal and communal attachment to the special urban form of the alley street.