Preliminary interplanetary trajectory designs frequently use simplified two-body orbital mechanics and linked conics methodology to model the complex trajectories in multi-body systems. Incorporating gravity assists provides highly efficient interplanetary trajectories, enabling otherwise infeasible spacecraft missions. Future missions may employ powered gravity assists, using a propulsive maneuver during the flyby, improving the overall trajectory performance. This dissertation provides a complete description and analysis of a new interplanetary trajectory design tool known as TRACT (TRAjectory Configuration Tool). TRACT is capable of modeling complex interplanetary trajectories, including multiple ballistic and/or powered gravity assists, deep space maneuvers, parking orbits, and other common maneuvers. TRACT utilizes an adaptable architecture of modular boundary value problem (BVP) algorithms for all trajectory segments. A bi-level optimization scheme is employed to reduce the number of optimization variables, simplifying the user provided trajectory information. The standardized optimization parameter set allows for easy use of TRACT with a variety of optimization algorithms and mission constraints. The dissertation also details new research in powered gravity assists. A review of literature on optimal powered gravity assists is presented, where many optimal solutions found are infeasible for realistic spacecraft missions. The need was identified for a mission feasible optimal powered gravity assist algorithm using only a single impulsive maneuver. The solution space was analyzed and a complete characterization was developed for solution types of the optimal single-impulse powered gravity assist. Using newfound solution space characteristics, an efficient and reliable optimal single-impulse powered gravity assist BVP algorithm was formulated. The mission constraints were strictly enforced, such as maintaining the closest approach above a minimum radius and below a maximum radius. An extension of the optimal powered gravity assist research is the development of a gravity assist BVP algorithm that utilizes an asymptote ΔV correction maneuver to produce ballistic gravity assist trajectory solutions. The efficient algorithm is tested with real interplanetary mission trajectory parameters and successfully converges upon ballistic gravity assists with improved performance compared to traditional methods. A hybrid approach is also presented, using the asymptote maneuver algorithm together with traditional gravity assist constraints to reach ballistic trajectory solutions more reliably, while improving computational performance.