WHITHER MUSIC? is a project that aims to establish model-based computer simulation (via methods of AI, (deep) Machine Learning and probabilistic modelling) as a viable methodology for asking questions about musical processes, developments, possibilities and alternatives - for music research, for didactic purposes, for creative music exploration scenarios. Computer simulation here means the design of predictive or generative computational models of music (of certain styles), learned from large corpora, and their purposeful and skilful application to answer, e.g., "what if" questions, make testable predictions, or generate musical material for further analysis, musicological or aesthetic. We believe that this would open new possibilities for music research, education, and for creative engagement with music, some of which will be further explored in the project.