An experimental study and modeling of the behavior of wood during compression along the fibers was carried out. The nonlinear analytical dependence of the load on the strain was considered. Attention was focused on the post-peak stage of deformation in order to determine the load and displacement at which the transition to the stage of plastic deformation occurs. The work was aimed at substantiating the application of the energy criterion of brittle fracture as a criterion for the transition to the stage of plastic deformation. To achieve this goal, methods of mathematical modeling and analysis of test results were used. As an upshot, a simple and practical procedure was developed to predict the transition point to the above stage of plastic deformation. The simulation results were consistent with laboratory tests of samples and fragments of structures. The practical significance of this criterion lies in its possible use as an additional tool for analyzing the condition of some wooden structures. Energy criteria, including the one mentioned above, belong to fairly universal criteria. Accordingly, the research methodology can be adapted to analyze the behavior of, for example, composites under other types of loads in further studies.