Urban art festivals are of great importance to strengthen the social and cultural life of communities, as they provide people with the opportunity to meet and enjoy various forms of creative expression, such as art, music, and dance, and also stimulate citizen participation. Evaluating the cultural and social impact generated by these festivals is essential to understanding their process and development, seeking future improvements, and ensuring their sustainability over time. For this reason, we have focused on the evaluation of the Callegenera Urban Expressions Festival, which has been held uninterruptedly in Monterrey, Mexico, from 2011 to 2022. Through qualitative research with in-depth interviews and life stories, the festival was explored as a space of introspection where boundaries are blurred to make room for art. We examined the emotional state of urban artists and graffiti writers, as well as the creative process through the intervention of space and economic aspects. In this way, we sought to understand the impact that this festival can have on the growth of the metropolitan area and its surroundings.