In order to analyze the influence of different elements on the stability of high speed cylindrical grinding process with CFRP grinding wheel, the Timoshenko beam theory was used to conduct the dynamic analysis on the stepped workpiece. Combined with the dynamic characteristics of grinding wheel measured by impact test, the grinding stability analysis of the two-degree-of-freedom system between grinding wheel and workpiece in high speed grinding process was conducted. During the dynamic analysis of the stepped workpiece, it was found that the stepped feature of workpiece has a small influence on the dynamic characteristics whose error is lower than 2%. In the grinding stability analysis, it was observed that the grinding stability can be affected by both the speed difference of grinding wheel and the difference of cutting position. The closer the grinding position is to the center of workpiece, the lower the grinding stability is and it is easy to induce chatter. As for the position near the center support, the grinding stability will be influenced by the dynamic performance of workpiece and grinding wheel at the same time as the increase of workpiece stiffness. The effectiveness of the proposed analytical method has been proved by the grinding experiment. The experiment results also indicate that the stiffness difference of the workpiece in different grinding positions can affect the surface quality, and the increase of workpiece surface roughness can reach 51.6% due to grinding instability.