How do I bend a plane and keep the objects on it following its bend? I want to to place some objects on a plane (for right now I'll keep it simple and say they're cubes). Then I want to bend that plane but keep the cubes connected to the plane, following the curve of the bend. Also I want to keep the cubes separate and not a part of the plane so I can edit them separately. A good example I can think of that represents what I want to do is the game Animal Crossing. 

Here's a screenshot of the game.

Is there any way I could go about doing this?
In edit mode subdivide the plane so to have a grid with enough vertices that will define the position of your cube, then select the 3 vertices nearest the position you want the cube to stay.

Then in object mode select the cube, Shift
 select the plane, press Ctrl+P
 and choose "vertex triangle", so the cube will always follow the average location of the three vertices of the plane.