Urban experimentation has been increasingly applied as a tool for finding new ways to face grand societal and environmental challenges⁠. Social learning and reflectivity that urban experiments might trigger are seen as crucial mechanisms in this process⁠. Nevertheless, it often remains unclear how to concretely enable learning in urban experimentation⁠. In order to address this practice and knowledge gap, an Experiential Learning and Transition Strategy (ELTS) was developed and applied to the Dutch mobile city experiments program (IMS)⁠. Its main aim was to foster learning within and beyond the experiment program boundaries⁠. Applying and assessing ELTS to IMS gave a clearer idea of what works (e⁠.g⁠., the use of learning exercises or guiding questions, stimulating “self-learning,” strong moderation, enough time, and a diverse group of participants), and what does not work (e⁠.g⁠., input from individual experts), when organizing learning events related to urban experimentation⁠.