The fate of the Jardim Colombo favela in São Paulo changed with the birth of a youth-led urban movement during the first art festival held in 2018. Planned and delivered in one month, the festival gathered dozens of volunteers and hundreds of residents to dream together about transforming a dumping site into a park for the community. The excitement of this initial action soon materialized into a self-aware social infrastructure ready to face future and unexpected challenges—including a pandemic, to which the young leaders in Jardim Colombo would respond with creativity, preventing devastating health outcomes. Drawing on three months of fieldwork and an ongoing relationship with the community leaders, I explore how this one-off celebration turned into an urban movement that is pursuing increasingly ambitious social and material goals. Sustained by four pillars—youth, women, creativity and planning—I present this story as a deployment of celebratory insurgency strategically engaging in festive practices to subtly push its counter-hegemonic political agenda in relation to cultural and identity matters. I argue that framing this creative approach as a planned urban celebration may inspire other planning initiatives seeking social justice in the peripheries of cities across the global South.