Unroll pie crust on lightly floured surface. Cut out 36 shapes at least 2? wide.
Place a level tsp of cherry pie filling into center of 18 shapes. Place on an ungreased baking sheet at least two inches apart. Brush outside edge of shape with milk. Place the other 18 shapes on top, and using the tines of a fork seal the edges shut.
Brush tops with more milk, and sprinkle with sugar. Bake for 12-15 minutes or until golden brown.
Remove with spatula (do not pick up by sticks yet) to cool on a wire rack.
Meanwhile, heat dipping chocolates according to package instructions. Dip edge of cooled pie pop into chocolate, and place on a sheet of wax paper to dry. Cover with sprinkles if desired.