The majority of mechanical parts are manufactured by milling machines. Hence, geometrically efficient algorithms for tool path generation and physical considerations for better machining productivity with guarantee of machining safety are the most important issues in milling tasks. In this paper, an optimized path generation algorithm for direction parallel milling which is commonly used in the roughing stage is presented. First of all, a geometrically efficient tool path generation algorithm using an intersection points-graph is introduced. Although the direction parallel tool path obtained from geometric information have been successful to make desirable shape, it seldom consider physical process concerns like cutting forces and chatters. In order to cope with these problems, an optimized tool path, which maintains constant MRR in order to achieve constant cutting forces and to avoid chatter vibrations at all time, is introduced and the result is verified. Additional tool path segments are appended to the basic tool path by using a pixel based simulation technique. The algorithm has been implemented for two dimensional contiguous end milling operations, and cutting tests are conducted by measuring spindle current, which reflects machining situations, to verify the significance of the proposed method.