This paper explores how engaging in and with philosophy in the streets has unique and special potential for children doing philosophy both inside and outside the classroom. We highlight techniques drawn from research into the political, social and activist potential of street art, and we illustrate how to apply these techniques in a P4C context in what we call guerrilla philosophy. We argue that guerrilla philosophy is a pedagogically powerful method to philosophically engage students whose ages range from 11-13. In calling attention to the power of guerrilla philosophy to engage students philosophically, we are tacitly assuming a Deweyan philosophical approach (Dewey 1916, 1925, 1934), which emphasises (1) the importance of promoting civic-mindedness as a social value; (2) the reliance on imaginative, creative and experiential forms of learning as essential to education ; and (3) a vision of the classroom as an embodiment of the larger civic community to which we all belong and in which we all must cooperate and engage (Dewey 1916). This paper traces these three themes in Dewey’s philosophical views of education and democracy, and considers how they are given a twenty-first century interpretation through street art, guerrilla philosophy and children’s activism.