A significant amount of time and energy is required to dry green timber with a large cross-section. Due to long-lasting internal moisture gradients, internal stress is high during the drying of large cross-sectional timber, and the potential for check occurrence is significant. Although many researchers have aimed to develop a method for drying large pieces of wood without the occurrence of drying defects, a procedure for rapidly drying wood without cracks has not yet been developed. In the present study, an outer surface sealing method and center-boring process (i.e., drilling a hole along the central longitudinal axis) was developed to dry timber with a large cross-section without the occurrence of checks. The proposed center-boring procedure reduces the movement of heat and moisture inside the wood and expedites the drying process by sustaining a small MC gradient. Moreover, the outer surface sealing treatment changes the drying stress direction and controls check occurrence. By kiln drying center-bored (80-mm diameter) and outer-surface-sealed round timber pitch pine (Pinus rigida) with an initial MC of 30% and an outer diameter of 140 mm, a final MC of 6% was obtained within 40 hours without the occurrence of any drying defects.