This paper considers local activists’ efforts to initiate public discussions about contested territories in St. Petersburg, and to resist political decisions about their (re)development. It also questions to what degree such grassroots efforts become political and analyzes different contexts of, and barriers to, politicization. By complementing sociological theorization about civic engagement and civic participation with French pragmatism, we examine how these activists constantly shift between informal, context-specific forms of protest and more institutionalized and politicized ones. Using a case-study approach, we describe and compare two recent conflicts in St. Petersburg where local residents resisted (re)development projects imposed by political and economic elites: the defense of the Yurgens House in the historic city center against its expected demolition, and the protest against renovation in Alexandrino, a park area on the city’s periphery. Our analysis is based on semi-structured interviews with local activists, participant and non-participant observation at public rallies and other gatherings, and qualitative analysis of protesters’ communication practices on social networks. We demonstrate that external political and social constraints encourage activists to be flexible in their forms of engagement, deploying a wide repertoire of tools of contestation: using local knowledge tactically, operating rationally within legal frameworks, and addressing broad audiences in search of public justification and support. We conclude that, whether these local activists remain at the level of informal place-based initiatives or opt for more institutionalized and professionalized forms of civic participation, they insistently reject claims that their efforts have a political rationale.