The emergence of non-trivial structure in many-body physics has been a central topic of research bearing on many branches of science. Important recent work has explored the non-equilibrium quantum dynamics of closed many-body systems. Photonic systems offer a unique platform for the study of open quantum systems. We report here the experimental observation of a novel dissipation driven dynamical localization transition of strongly correlated photons in an extended superconducting circuit. Monitoring the homodyne signal reveals this transition to be from a regime of classical oscillations into a macroscopically self-trapped state manifesting revivals, a fundamentally quantum phenomenon. This experiment also demonstrates a new class of scalable quantum simulators with well controlled coherent and dissipative dynamics suited to the study of quantum many-body phenomena out of equilibrium.