In various engineering applications, self-tapping screws are used to connect timber members. To describe their load-deformation relationship, a better understanding of the strain along the mechanical interface (i.e., timber-screw interface) is required. With a focus on the axial loading of self-tapping screws, only a few studies have dealt with the determination of the strain based on optical measurement techniques. Therefore, in the present study, the strain distribution at the timber-screw interface was monitored during pull-out tests using an optical measurement technique, called electronic speckle pattern interferometry (ESPI). Strains obtained from the ESPI measurements were compared with the results obtained from structural simulations conducted with finite element modelling (FEM). Three different types of solid spruce wood (Picea abies (L.) Karst.) specimens with different grain orientations connected with self-tapping screws (thread length lg = 130 mm, outer thread diameter d = 12 mm) were tested in withdrawal. There was a good agreement between the ESPI and FEM results, confirming that ESPI was a suitable measurement technique. The study also provided insights and results regarding the region of strain concentrations across the length of self-tapping screws.