Masonry is an ancient and heterogeneous construction material with complex local failure modes. The random and nonlinear nature of masonry’s response to mechanical loading provides hurdles in understanding and predicting masonry behaviour and failure. With elongated design lives, global count in ageing masonry structures is increasing. Masonry’s continued usage even in visibly deteriorated states raises the importance of regular, non-destructive assessment of masonry structural health. Particle-based Discrete Element Method (pbDEM) is an analytical technique proven to accurately replicate fracture pathways and failure behaviour of brittle materials, at the scale of grains. This investigation applies the pbDEM to model masonry behaviour and is validated against a physical test applying a short-term mechanical loading scenario found in literature. Results show high levels of accuracy in peak stress and stiffness replication, with promising signs for this application to be expanded into investigating relevant issues related to masonry behaviour.