The behavior of the dry-stone masonry retaining structure has been investigated via physical model test and numerical simulation. In the model test, the digital image analysis using PIV technique was employed to measure horizontal displacements in the backfill soils and retaining blocks. For finite element numerical analyses, the commercial code, ABAQUS, was used. The horizontal displacements observed in the model test showed that the development of the failure surface is progressive. Numerical results showed that in most cases horizontal earth pressure is distributed similarly to a conventional Rankine’s distribution. However, lower values of the internal friction angle of the backfill soils and interface friction angle in the front blocks produce irregularly nonlinear distribution of the horizontal earth pressure.