The goal of this study was to analyze the bearing properties of the differently oriented glulam using digital image correlation (DIC). Six differently oriented specimens associated with three anatomical directions including longitudinal (L), radial (R), and tangential (T), and 12-mm drift pins were used to analyze the bearing properties, including yield load and bearing strength. The highest bearing strength of 22.57 MPa from RL was found, whereas the lowest bearing strength of 6.47 MPa from LR was found. Different strain distributions were observed from the differently oriented bearing specimens using DIC. Different failure ratios of the differently oriented specimens were highly related to the strain distributions. Although the bearing properties were found to be different between the differently oriented specimens, for the connection design aspect, the bearing properties of glulam could be grouped as RL and TL specimens, RT and TR specimens, and LR and LT specimens.