Finding the best toolpath planning strategy for Computer Numerical Control (CNC) machining requires a trial-and-error approach. One needs to follow a number of steps, viz., generate the toolpath, perform simulations/machining, measure various parameters to quantify the quality of the toolpath, and then select the best toolpath. This conventional iterative approach is time-consuming and often error-prone. This paper presents a novel Machine Learning based system for choosing the best toolpath planning strategy for CNC machining (finishing) of complex freeform surfaces directly from the CAD model. Three tool path planning strategies are considered, viz. Adaptive planar, Iso-scallop, and Hybrid. At first, a novel toolpath analysis module is presented to evaluate the quality of the toolpath considering performance parameters such as the surface finish, toolpath length, and smoothness. The toolpath analysis module was extensively tested for robustness and accuracy. This quality measurement technique is then used to analyze and label a large number of CAD models to create a dataset for supervised learning for the three toolpath strategies. A Convolutional Neural Network (CNN) model is designed to predict the best toolpath planning strategy. Results show that the proposed data-driven model achieved 96.8% test accuracy.