Planning of optimal toolpath, cutter orientation, and feed rate for 5-axis Computer Numerical Control (CNC) machining of curved surfaces using a flat-end mill is a challenging task, although the approach has a great potential for much improved machining efficiency and surface quality of the finished part. This research combines and introduces several key enabling techniques for curved surface machining using 5-axis milling and a flat end cutter to achieve maximum machining efficiency and best surface quality, and to overcome some of the key drawbacks of 5-axis milling machine and flat end cutter use. First, this work proposes an optimal toolpath generation method by machining the curved surface patch-by-patch, considering surface normal variations using a fuzzy clustering technique. This method allows faster CNC machining with reduced slow angular motion of tool rotational axes and reduces sharp cutter orientation changes. The optimal number of surface patches or surface point clusters is determined by minimizing the two rotation motions and simplifying the toolpaths. Secondly, an optimal tool orientation generation method based on the combination of the surface normal method for convex curved surfaces and Euler-Meusnier Sphere (EMS) method for concave curved surfaces without surface gouge in machining has been introduced to achieve the maximum machining efficiency and surface quality. The surface normal based cutter orientation planning method is used to obtain the closest curvature match and longest cutting edge;​ and the EMS method is applied to obtain the closest curvature match and to avoid local gouging by matching the largest cutter Euler-Meusnier sphere with the smallest Euler-Meusnier sphere of the machined surface at each cutter contact (CC) point. For surfaces with saddle shapes, selection of one of these two tool orientation determination methods is based on the direction of the CNC toolpath relative to the change of surface curvature. A Non-uniform rational basis spline (NURBS) surface with concave, convex, and saddle features is used to demonstrate these newly introduced methods. Thirdly, the tool based and the Tri-dexel workpiece based methods of chip volume and cutting force predictions for flat-end mills in 5-axis CNC machining have been explored for feed rate optimization to achieve the maximum material removal rate. A new approach called local parallel slice method which extends the Alpha Shape method - only for chip geometry and removal volume prediction has been introduced to predict instant cutting forces for dynamic feed rate optimization. The Tri-dexel workpiece model is created to get undeformed chip geometry, chip volume, and cutting forces by determining the intersections of the tool envelope and continuously updating the workpiece during machining. The comparison of these two approaches is made and several machining experiments are conducted to verify the simulation results. At last, the chip ploughing effects that become a more serious problem in micro-machining due to chip thickness not always being larger than the tool edge radius are also considered. It is a challenging task to avoid ploughing effects in micro-milling. A new model of 3D chip geometry is thus developed to calculate chip thickness and ploughing volume in micro 5-axis flat-end milling by considering the minimum chip thickness effects. The research forms the foundation of optimal toolpath, cutter orientation, cutting forces/volume calculations, and ploughing effects in 5-axis CNC machining of curved surfaces using a flat-end mill for further research and direct manufacturing applications.