Large-scale wind farm integration has brought several aspects of challenges to the transient stability of power systems. This paper focuses on the research of the transient stability of power systems incorporating with wind farms by utilizing risk assessment methods. The detailed model of double fed induction generator has been established. Wind penetration variation and multiple stochastic factors of power systems have been considered. Theprocess of transient stability risk assessment based on theMonte Carlo method has been described and a comprehensive risk indicator has been proposed. An investigation has been conducted into an improved 10-generator 39-bus system with a wind farm incorporated to verify the validity and feasibility of the risk assessment method proposed.