Many mechanical parts are manufactured by milling machines. Hence, geometrically efficient algorithms for tool path generation, along with physical considerations for better machining productivity with guaranteed machining safety, are the most important issues in milling. In this paper, an optimized path generation algorithm for direction-parallel milling, a process commonly used in the roughing stage as well as the finishing stage and based on an incomplete 2-manifold mesh model, namely, an inexact polyhedron widely used in recent commercialized CAM software systems, is presented. First of all, a geometrically efficient tool path generation algorithm using an intersection points-graph is introduced. Although the tool paths obtained from geometric information have been successful in forming desired shapes, physical process concerns such as cutting forces and chatters have seldom been considered. In order to cope with these problems, an optimized tool path that maintains a constant MRR for constant cutting forces and avoidance of chatter vibrations, is introduced, and verified experimental results are presented. Additional tool path segments are appended to the basic tool path by means of a pixel-based simulation technique. The algorithm was implemented for two-dimensional contiguous end milling operations with flat end mills, and cutting tests measured the spindle current, which reflects machining characteristics, to verify the proposed method.