Rouge cutting process takes the major portion of machining operation using NC milling machine. Especially, most of the machining time is spent in this process when molds are machined. Therefore, an efficient algorithm for generating the tool path for rough cutting is suggested in this paper. The first step of the procedure is getting the volume to be machined by applying the Boolean operation on the finished model and the workpiece which have been modeling system. Basic principle of determining machining procedure is that a large tool should be used at the portion of the simple shape while a small tool should be used at the complex portion. This principle is realized by representing the volume to be machined by an octree, which is basically a set of hexahedrons, and matching the proper tools with the given octants. When the tools are matched with the octants, the tool path can be derived at the same time.