As the penetration of wind power into the power system increases, the ability to assess the reliability impact of such interaction becomes more important. The composite reliability evaluations involving wind energy provide ample opportunities for assessing the benefits of different wind farm connection points. A connection to the weak area of the transmission network will require network reinforcement for absorbing the additional wind energy. Traditionally, the reinforcements are performed by constructing new transmission corridors. However, a new state-of-art technology such as the dynamic thermal rating (DTR) system, provides new reinforcement strategy and this requires new reliability assessment method. This paper demonstrates a methodology for assessing the cost and the reliability of a network reinforcement strategy by considering the DTR systems when large scale wind farms are connected to existing power network. Sequential Monte Carlo simulations were performed and all DTRs and wind speed were simulated using the auto-regressive moving average (ArMA) models.