A simple, compact, yet powerful robotic winch, called "Winch-Bot," is presented in this thesis. The Winch-Bot is an underactuated robot having only one controllable axis. Although hanging a load with merely one cable, it is capable of moving it in a large workspace by swinging the load dynamically based on parametric self-excitation. The generated trajectories can be used for a variety of tasks, from moving material to cyclic inspection of surfaces. The basic principle and design concept of the Winch-Bot are first described, followed by dynamic modeling and analysis. Two trajectory generation problems are solved. One is point-to-point transfer of a load, and the other is the tracking of a continuous path. It will be shown that the system can track a given geometric trajectory, although the tracking velocity cannot be determined arbitrarily due to the underactuated nature of dynamics. A prototype Winch-Bot is designed and built, and point-to-point, continuous path, and parametric excitation control are implemented.