What you do is make a scene containing the objects you want to outline. Go to top view, and enable distance mask in the render options. Render and you should get what looks like the hieght map for a terrain, which it will be. Save this image and make a new scene. Create a terrain and apply the saved image. Now in the main window multi-replicate a cube and then the result to get a grid. Resize the cube (or any other object) grid so it fits over the terrain in top view (the terrain should be slighter larger than the grid of objects.) Now turn the wireframe resolution for "static" to as high as it will go (the higher it is, the more accurate it is, but the longer it takes. Experiment) Now with all the individual cubes or other objects selected (they should all the above the terrain) go to the alignment tool (next to the resize tool) and from the dropdown menu select "drop to land." This drops the objects onto the outline of the terrain. You can paint your own terrains from scratch if you want, and try a few small applications of bryce's randomize feature to create irregularities such as those seen above.