Due to wood moisture sensitivity, shrinkage cracks tend to present wooden structures. These failures are caused by moisture-related shrinkage behavior. In order to avoid it, it is necessary to have a better understanding of shrinkage behavior. In this respect, studying the dimension changes in wood at different scales is of utmost significance for a better understanding of the shrinkage properties. Herein, the shrinkage behavior of Masson pines (Pinus massoniana) wood was investigated at macroscopic and cellular levels during moisture loss via digital image correlation using VIC-3D and digital microscopic systems, respectively. According to the full-field strain maps, shrinkage strain near the external face was higher than that at the internal face, which increased susceptibility to cracking at the external face of lumber. Additionally, the anisotropic shrinkage of wood was explored. The shrinkage ratio at the end of drying was about 5.5% in the tangential (T) direction and 3.5% in the radial (R) direction. However, at a cellular level, the shrinkage ratios in the T and R directions of earlywood tracheids were 7.13% and 2.46%, whereas the corresponding values for latewood tracheid were 9.27% and 5.52%, respectively. Furthermore, the maximum T/R shrinkage ratio at the macroscopic level (1.7) was found to be similar to the value of latewood tracheid (1.72). The earlywood showed high anisotropic, its T/R shrinkage ratio was 2.75. The macroscopic shrinkage was the result of the interaction of the tracheids of earlywood and latewood and was mainly dominated by latewood tracheids.