The increased presence of electric vehicle charging locations in a power system with high penetration of intermittent wind power potentially leads to operation complexities resulting in abnormal impacts. This paper proposes an innovative framework for assessing the impact of plug-in electric vehicle (PEV) charging locations on a power system with integrated wind farms, incorporating dynamic thermal limits (DTLs). The framework comprises Monte Carlo simulation, which is embedded with stochastic modeling of various uncertainties under the key operating conditions. As part of the modeling framework, the transmission lines are ranked in accordance with the lowest level of expected energy not supplied. The PEV charging demand is then modeled by incorporating DTLs and applied to the least stressed transmission lines, following the IEEE 738-2006 standard. The new assessment framework is investigated using an IEEE 24-bus test system. The results demonstrate that applying DTLs on the least stressed transmission lines in conjunction with the integration of decentralized wind farms and strategic charging location of PEVs significantly improves the security of the energy supply and considerably reduces interruption costs, as opposed to not having such a framework.