||5-axis machining enjoys tremendous advantages in terms of better tool accessibility, faster material removal rate, much improved surface finishing quality, among others. The solution to automatically generating collision-free tool paths has been studied for a number of years. Traditional methods in automatic 5-axis tool path generation require huge computing time to calculate the tool orientation to avoid gouging and global interferences. This thesis presents a collision-free 5-axis tool path generation system that uses a haptic device to perform real-time and reliable man-machine interactions. The system is based on commercial haptic devices which can provide 3 degrees of freedom (DOF) force feedback and 6 DOF posture sensing. The system achieves five main functions: (1) a rendering conversion that uses 3 DOF force feedback haptic representation instead of the 5 DOF real world requirements; (2) an efficient force feedback design that helps obtain accurate results directly from the user’s manipulation; (3) a fast collision detection scheme to achieve real time feedback; (4) a reduction of the user’s operation workload by providing heuristic leading forces; and (5) a comprehensive haptic design that supports both ball-end tools and flat-end tools with partial optimization. The system faithfully represents the real milling machining procedure both graphically and haptically. No matter whether an expert or not, the user is able to use the presented interactive system to conveniently plan and design collision-free 5-axis tool paths.