This paper elaborates a novel optimum programming-based algorithm that embeds the stochastic multiobjective particle swarm optimization (PSO) method and the deterministic interior point method to calculate the maximum wind power penetration level. With the optimization target of promoting the wind generation capacity, the three-stage optimization strategy is established to contemplate the transient stability constraint (TSC) as well as the uncertainty factors in the high wind penetrated system. To address the uncertainty factors in system, the chance-constrained optimization approach is practiced to figure out the initial optimal operating point in the first stage. On the ground of which, the TSC is reinforced in the second stage to delineate the dynamic feasible region. Among the obtained security domain, the ultimate operation solution is calculated in the last stage and provides operators with specific operating scheme. The framework is capable of supporting alternative optimal methods and can be extended to more complex system modeling. The feasibility of the algorithm framework has been demonstrated by simulations on two benchmark systems. And it has prosperous application prospects for optimization problems that need to consider system dynamic security and uncertainty simultaneously.