This paper discusses the impacts of large scale grid-connected wind farm equipped with permanent magnet synchronous generator (PMSG) on power system small signal stability (SSS) incorporating wind generation uncertainty and volatility. Firstly, a practical simplified PMSG model with rotor-flux-oriented control strategy applied is derived. In modeling PMSG generator side converter, the generator-voltage-oriented control strategy is utilized to implement the decoupled control of active and reactive power output. In modeling PMSG grid side converter, the grid-voltage-oriented control strategy is applied to realize the control of DC link voltage and the reactive power regulation. Based on the Weibull distribution of wind speed, the Monte Carlo simulation technique based is carried out on the IEEE 16-generator-68-bus test system as benchmark to study the impacts of wind generation uncertainty and volatility on small signal stability. Finally, some preliminary conclusions and comments are given.