High-flying unmanned reconnaissance and surveillance systems are now being used extensively in the United States military. Current development programs are producing demonstrations of next-generation unmanned flight systems that are designed to perform combat missions. Their use in first-strike combat operations will dictate operations in densely cluttered environments that include unknown obstacles and threats, and will require the use of terrain for masking. The demand for autonomy of operations in such environments dictates the need for advanced trajectory optimization capabilities. In addition, the ability to coordinate the movements of more than one aircraft in the same area is an emerging challenge. This thesis examines using an analytical reduced order formulation for trajectory generation for minimum time and terrain masking cases. First, pseudo-3D constant velocity equations of motion are used for path planning for a single vehicle. In addition, the inclusion of winds, moving targets and moving threats is considered. Then, this formulation is increased to using 3D equations of motion, both with a constant velocity and with a simplified varying velocity model. Next, the constant velocity equations of motion are expanded to include the simultaneous path planning of an unspecified number of vehicles, for both aircraft avoidance situations and formation flight cases.