Draw faces on each one of the pumpkins with a pencil. Cut into your pumpkins and cut out the faces using a Dremel tool.
Use the sanding drum attachment to sand out the inside of the teeth, nose, and eyes. Erase any remaining pencil lines.
Place two pieces of scrap 2 x 4s in the bottom of the planter in an "X."
Use a drill with a 1" spade bit to place two holes - one in each scrap on top of each other - into the wood. Stick the dowel rod through both pieces, down into the planter.
Pack potting soil into the planter tightly, covering the wood and stabilizing the dowel rod.
Spread hay into the planter around the base for a fun fall look.
Use the 1" spade bit to drill three holes in each pumpkin. Tilt them at angles and make a hole at the top and bottom for the dowel, then cut a hole in the back to insert the lights.
Slide each pumpkin down onto the dowel rod.
Place one light strand in the back of each pumpkin, leaving both ends hanging out.
Cut a circular piece of black Duck Tape with a slit in it. Place over the hole with the parts of the light strand hanging out that you want to attach.
Place the topiary near a light outlet and plug in to light.