An urge to make cities more livable, variable, and vibrant has become an accepted trend in many world cities, pursued by politicians as well as urban activists and dwellers. This is no less true for the post-Soviet cities, where top-down urban planning is still in power, while bottom-up initiatives are rising, as it is in St.Petersburg, Russia, the context of this study. Forced to action by existing inconsistencies in the quality of urban environment and supported by incoming knowledge from European cities on community driven, bottom-up, and participatory approach, these initiatives aim at physical and conceptual transformation of the city using artistic, design and cultural means. We are labeling such initiatives ‘creative’ meaning here grassroots creativity as opposed to the planned one, and regarding as creative these initiatives’ innovative and unconventional approach to the urban environment and unique artifacts, events and texts they produce. Based on the observations and interviews with 10 such initiatives in St.Petersburg we analyze their social structure, often of multidisciplinary character comprising architects, urban designers, social scientists, and artists. We consider the foundations of these communities’ solidarity and enthusiasm which is often of volunteer nature, at least, in the beginning of their activity, when most of them start as informal groups of like-minded friends. We consider the value system of the communities, which predominantly has a critical impulse questioning the norms of public institutions regulating urban development as well as everyday life in the city. In the paper we also classify the formats in which communities re-think and re-make the city during their artistic, cultural and pedagogical projects. Creative initiatives also act in different environments and try to reconsider dullness, closedness and one-dimensionality of the open urban spaces (streets, squares, parks, etc); junk and transit spaces; post industrial sites; semi-private locations and recreate them into spots of emotional attraction, self-expression, and creativity as well as locations for new economies. At last, we dwell upon the risks of these initiatives’ future in view of their precarity and foresee several paths for their collective career.