Prepare orange candy coating according to package directions. Carefully twist apart sandwich cookies and lay out on baking sheet lined with waxed paper. Using a lollipop stick or straw, make an indentation into the filling of each cookie. Dip the end of a lollipop stick or straw into the candy coating, covering about 1” of the stick in the candy coating, and then gently press it into the indentation in the filling of a cookie. Place 1 to 2 teaspoons of additional candy coating onto the top of the stick where it is pressed into the filling. Place the top of the cookie back onto the cookie. Repeat with remaining cookies, then carefully place into the refrigerator to chill for at least 15 minutes.
Unrwap Tootsie Roll® Chocolate Midgee candies. Using a small roller, roll out candies to roughly 1/4 inch thick. Using either a small knife or cookie cutter, cut candy into 24 small triangle shapes to create jack o’ lantern eyes.
If needed, reheat candy coating according to package directions. Working one cookie at a time, remove cookie from refrigerator and holding the stick, dip the cookie into candy coating, completely covering cookie by dipping and spooning candy coating over cookie. Let excess candy coating drip off of cookie and back into container. Place cookie onto a baking sheet lined with wax paper. Immediately place two chocolate triangle eyes onto cookie and place mini chocolate chips onto cookie to create a nose and mouth. Repeat with remaining cookies and allow to dry for at least one hour.
Prepare black candy writer pen according to package directions. Squeeze a dollop of black candy coating, approximately the size of a penny, onto the top of a cookie pop. Sprinkle rainbow colored sprinkles over candy coating. Squeeze two additional small dollops of black candy coating onto both sides of the rainbow sprinkles. Place a piece of black licorice onto the top of the cookie, with ends in dollops of black candy coating, to create a handle. Hold in place until candy coating starts to set and can hold licorice on it’s own. Place on a baking sheet covered in wax paper to dry for at least two hours. Repeat with remaining cookies.