We suggest that planning for automated earthmoving operations such as digging a foundation or leveling a mound of soil, be treated at multiple levels. In a system that we have developed, a coarse-level planner is used to tessellate the volume to be excavated into smaller pieces that are sequenced in order to complete the task efficiently. Each of the smaller volumes is treated with a refined planner that selects digging actions based on constraint optimization over the space of prototypical digging actions. We discuss planners and the associated representations for two types of earthmoving machines: an excavator backhoe and a wheel loader. Experimental results from a full-scale automated excavator and simulated wheel loader are presented.