Estimates suggest that tens of millions of people skateboard for transport and pleasure‚ÄövÑvÆit is a mobility practice both instrumental and playful. That play is important for creativity, connection, and positive affect is known. Yet skating is often typified as mere vandalism, despite the fact that, intrinsic worth aside, its hybridity is instructive: It invites consideration of the spatial politics of the street and the possibility of accommodating this and, indeed, other forms of alternative‚ÄövÑvp movement. Arguably, the prospect of such generous geographies is fundamental to ideas about the right to the city, an entitlement embracing responsibilities to one another. Nevertheless, given the ongoing dominance of automobility and widespread anxieties about skating, the tendency has been to try and contain it in parks and regulate its presence on streets, not least by creating design solutions to render it difficult to engage in. A corollary of these strategies, in combination with skaters' own resolve to claim rights to the city, is that skaters move on to roadways. These armatures have not been designed generously to accommodate forms of mobility apart from motor vehicles‚ÄövÑvÆand sometimes pedestrians and cyclists. Consequently, skaters are among the millions who die on the roads annually. In relative terms, the number is minute; nevertheless, each death invokes this question: How can we mobilize a spatial politics of street skating by thinking about the geographies of generosity in ways that might avoid such events? Reflecting on that question is the purpose of this article.