Start with a cylinder

 (this one is on a board with a used piece of sandpaper stapled to it)

The sand paper helps keep the ice from spinning

Using a Vee bit make a shallow hole in the middle

Using a Hole Drill, Drill down about 6 inches

Using your hand remove most of the snow

Using a 1/4" end mill, make a drainage hole

Here a bottle holder is frozen to the top of a logo