ShapedTools

This allows players to create pickaxes in a variety of configurations (e.g. a 1x1x2 pickaxe, a 1x3x3 pickaxe, a 1x3x2 pickaxe, and a 3x3x3 pickaxe). The idea behind this plugin is to speed up the task of mining without otherwise changing the flow of resources. Enchantments, damage, and other properties are carried through to the upgraded pickaxe.

Recipes (done with diamond but applicable to any material except wood):
1x1x2 Top Drill (will break the block above the one being mined, regardless of orientation):

1x1x2 Bottom Drill (will break the block below the one being mined, regardless of orientation):

1x3x3 Hammer (will break all blocks surrounding the one being mined, sensitive to orientation):

Upgrading:

Upgrading can only be done to diamond and iron pickaxes and is done by putting blocks of the material as seen above. This adds a depth dimension to the mining. So an upgraded Hammer will destroy a 3x3x3 area. An upgraded drill will destroy a 1x2x3 area.