CUPCAKES: Heat oven to 350 degrees. Line two 12 count muffin pans with 24 cupcake cups.
In large bowl, beat cake mix, pumpkin, water, oil, eggs, and pumpkin pie spice with an electric mixer on low speed for 30 seconds, then on medium speed for 2 minutes, scraping the bowl occasionally. Divide batter evenly among cupcake cups (about two-thirds full).
Bake 18 to 22 minutes or until a toothpick inserted in center comes out clean. Cool in pans for 10 minutes; remove cupcakes from pans to a cooling rack. Cool completely, about 30 minutes.
ORANGE CREAM FROSTING: Beat softened cream cheese and butter together until smooth and creamy. Gradually add confectioners’ sugar, beating after each addition. Add orange extract and food coloring until you get the perfect pumpkin color.
Fill a piping bag fitted with a 2D or 1M tip; pipe frosting onto cupcakes.
Mold each Tootsie Roll into a "stem." Cut each Watermelon Air Heads in half, mold into a "vine" by rolling between your palms into a 3-inch rope and then twist the rope to shape into a vine.