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Transient stability is a major concern in power system security and reliability because it is the most common type of instability and its impacts can cause greatest economic losses. For enhancing the energy security, it requires the power system operation to be evaluated during both the planning and the operation stage. Many online/offline transient stability assessment techniques have already been developed for this purpose. However, due to the increase in energy demand, the modern power system has grown to a very sophisticated and large system for which extent transient stability assessment methods may not be able to handle. In addition, the new published regulation rules and new concepts such as the smart grid have also pushed the requirement for transient stability assessment to a higher level. Thus, this dissertation is intended to study large scale power system transient stability. It starts from establishing an analytical approach for power system transient stability assessment. Based on the results, the disadvantages of traditional concepts used in transient stability assessment have been discussed. In order to overcome the difficulties encountered by classical approaches, a new technique for estimating the generator rotor angle difference in multi-machine power system is developed. It is more practical and has been applied to study the impact of wind power generation on power system transient stability afterwards. Since recently there is a significant increase in the importance of renewable energy and its related optimizations in power systems, the final goal of this dissertation focuses on the power system optimal power flow technique with wind power penetration and transient stability constrains. For making results more convincible, the South Carolina offshore wind speed data is used as the availability of wind power. An approach for maintaining the power system economic operation within the security range has been given at the end of this dissertation.