Contour parallel tool paths are among the most widely used tool paths for planer milling operations. A number of exact as well as approximate methods are available for offsetting a closed boundary in order to generate a contour parallel tool path; however, the applicability of various offsetting methods is restricted because of limitations in dealing with pocket geometry with and without islands, the high computational costs, and numerical errors. Generation of cusps, segmentation of rarefied corners, and self-intersection during the offsetting operations and finding a unique offsetting solution for pocket with islands are among the associated problems in contour tool path generation. Most of methods are inherently incapable of dealing with such problems and use complex computational routines to identify and rectify these problems. Also, these rectifying techniques are heavily dependent on the type of geometry, and hence, the application of these techniques for arbitrary boundary conditions is limited and prone to errors. In this paper, a new mathematical method for generation of contour parallel tool paths is proposed which is inherently capable of dealing with the aforementioned problems. The method is based on a boundary value formulation of the offsetting problem and a fast marching method based solution for tool path generation. This method handles the topological changes during offsetting naturally and deals with the generation of discontinuities in the slopes by including an "entropy condition" in its numerical implementation. The appropriate modifications are carried out to achieve higher accuracy for milling operations. A number of examples are presented, and computational issues are discussed for tool path generation.