The paper analyzes the urban transformation and the development of criteria for the conception and design of outdoor urban space, in the smart city context. In the regeneration of peripheral historical and postindustrial neighborhoods, interactive storytelling and cultural mediation forcollaborative placemakingof public sites can generate not only art and culture - in accordance with the enhancement of historical memory and to the rediscovery of local identity - but also opportunities for redevelopment. The research evaluates case studies and explores the potential of innovative micro-community aggregation through the social media interaction, the analysis of use and performance requirements for public space and the experimentation offrom the bottomconstruction of new services and equipment through an interdisciplinary collaborative network. The network promises constituted by citizens, community facilitators, professional experts, young in training creative and local artisan entrepreneurs. The collaborative placemaking focuses on the design and construction of eco-friendly and recycling equipment and on the sharing services for the use of marginal outdoor spaces and the re-use of abandoned spaces on the ground floor of buildings. The plan of operations research is to establish acreative supply chain, from the development of a web platform for sharing spatial data and a "map of the community" to the construction of hybrid places - real and digital - through processes of traditional handcrafts such as digital fabrication, to improve the quality of living, the leisure and the health.