Dry stone retaining walls (DSRWs) are vernacular structures, which consist in a specific assemblage of individual rubble stones. Herein, we propose some recommendations to achieve a correct modelling of the mechanical behaviour of DSRWs towards failure with the use of the Discrete Element Method (DEM). There are two kinds of DSRWs, those that just retain slope and others that retain a road built on the top of the backfill. For walls retaining slopes, a full 2D DEM approach (PFC2D) was used as the most sophisticated way to study such a system and the modelling was validated on full scale experiments. The modelling retrieved in a very good way the features observed on site as the expense of much computation time. More interesting was the use of a mixed DEMcontinuum approach (UDEC) where the constitutive laws for the stone-stone contact and backfill-wall contact are averaged. Very efficient in terms of computation time, the process of identification of the model parameters is here much lighter than with a full DEM approach without losing precision for the prediction. For walls retaining a slope with a highway a mixed 3D DEM-continuum approach (3DEC) was required. A straightforward methodology was proposed in order to correctly retrieve the features observed in both scaled down experiments or in full scale experiments. In conclusion, the full DEM and the mixed DEM-continuum approaches were able to precisely capture the mechanical behaviour of DSRWs towards failure even if idealised blocks were used.