Ten designers were invited to imagine a possible transformation (real or metaphorical) of the Cimiano neighborhood through a graphic representation and a short text. “La Quinta Stagione” (literally “The Fifth Season”) is a metaphor for a renewed environmental dimension, a possible design space capable of incubating regenerative practices and inclusive activities for the communities that inhabit it. The places, symbols, architecture, people, animals, and rituals of the neighborhood constitute a perennial season in constant change capable of acting on reality and transformations.