Following the ideas of such writers as Florida, Landry and others on the ‘creative city’ and the ‘creative class’, creativity is now widely acknowledged to be a trigger for innovations and urban development. However, these ideas put the main accent on macro-level analysis, i.e. the economic effects of creativity in cities. The micro-level of creativity—grass-roots interactions of real creative actors, which form the immediate context for ideas generation and active involvement in urban life—has not been given due consideration. The micro-level of creativity, emerging through the every day practices of ‘creative’ people becomes even more valuable in the urban contexts characteristic of the post-Soviet region, where there are minimal policies to support contemporary creativity. Limited governmental support for creative clusters, cultural industries and artistic initiatives draws attention to the various adaptation tactics used by urban creative actors. In this chapter I analyze three artistic communities based in St. Petersburg, Russia, working in the sphere of contemporary art. I show the ways in which artists deal with the challenges characteristic of the field of contemporary art in the city, in particular, the lack of contemporary art education, insufficient number of experts in the sphere of contemporary art, and the scarcity of infrastructure for contemporary artists. Artists are able to partly overcome these challenges by forming independent artistic communities and performing various practices of localization, representation, functional division and communication. In this way they contribute to bottom-up development of the contemporary art sphere in the city. Artistic communities eventually become one of the main social actor groups who form urban ‘cultural capital’—the grounding for contemporary creativity in St. Petersburg—which is not being developed through the city’s local government policies.