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Halloween Chocolate Cupcakes

Chocolate Cupcakes with Tootsie Roll Goblins

Don't let these goblin cupcakes scare you too much, you can take a bite out of them and they wont bite back.
Course Dessert
Cuisine American
Keyword Halloween Chocolate Cupcakes
Prep Time 45 minutes
Cook Time 30 minutes
(Cooling Time Not Included In Total Time) 1 hour
Total Time 1 hour 15 minutes
Servings 30 (Makes about 30 cupcakes)


For the Goblins and Scary Trees:

  • 15 Tootsie Roll Flavor Roll Candies Various Colors
  • 10 ounces Chocolate candy coating 5 squares of Almond Bark
  • 60 Candy eyeballs
  • Wax paper

For the Cupcakes:*

  • 2 cups sugar
  • 1-3/4 cup flour
  • 3/4 cup unsweetened cocoa powder
  • 1-1/2 teaspoon baking powder
  • 1-1/2 teaspoon baking soda
  • 1 teaspoon salt
  • 2 eggs
  • 1 cup milk
  • 1/2 cup canola oil
  • 2 teaspoons vanilla extract
  • 1/2 cup boiling water

For the Frosting:*

  • 1/2 cup butter 1 stick
  • 2/3 cup unsweetened cocoa
  • 3 cups powdered sugar
  • 1/3 cup milk
  • 1 teaspoon vanilla extract


For the Goblins and Scary Trees:

  • Start by making the Goblin faces;  Lay a sheet of wax paper on a large flat plate or cookie sheet. Set aside.
  • Unwrap the Tootsie Rolls. With your fingers flatten out the Tootsie Roll into a rounded rectangle-type shape.
  • With the tip of a knife make small holes for the eyes and nose. Next, make a small cut for the mouth. Lastly, gently stretch it out to make a ghost-like face. Set the Goblin faces on the wax paper and set aside.
  • Next, make the chocolate background for the Goblin faces; lay another piece of wax paper over a cookie sheet (or large flat plate).
  • Put the candy coating in a small bowl and melt it in the microwave for about 30 seconds.  Use the back of a small spoon to spread the chocolate on to the wax paper in an oval shape that is a little bit large than the goblin faces.
  • Then lay a Goblin face over the chocolate and gently push it down so the chocolate seeps through the eyes, nose and mouth. Then add the eye balls so that they touch the chocolate that is seeping out of the eye holes of the Tootsie Roll. Repeat this process for each Goblin face.
  • Then, make the scary trees; Lay a long piece of wax paper on to a large flat plate or cookie sheet. Set aside for a moment.
  • Add more chocolate coating to the chocolate bowl and melt it for 30 seconds. Stir until creamy.
  • Dip a small spoon in the melted chocolate, and on the wax paper draw a tree trunk. Dip the spoon back in the melted chocolate and add branches to the tree trunk. While the chocolate is still warm and soft, add candy eyeballs randomly on the tree to make it look scary.
  • Repeat the process to make more trees. But make them one at a time so that the chocolate is soft when it's time to put the candy eyeballs on the tree.
  • Put the plates/cookie pans with the chocolate goblins and scary trees in the refrigerator to chill while the cupcakes are being made, baked and cooled.

For the Cupcakes:

  • Preheat oven to 350 degrees F.  In a large bowl, combine the dry ingredients. Set aside.  In a medium size bowl, combine the eggs, milk, canola oil, and vanilla extract.
  • Whisk together the egg mixture. Add the egg mixture to the dry ingredients. With a large spoon, stir all of the ingredients together a few times so that the flour and cocoa powder don’t create dust when using a hand mixer.
  • Beat the mixture on medium speed for about 2 minutes.  Pour in the boiling water (an easy way to heat the water is in a mug in the microwave).
  • Line the cupcake tin with paper baking cups. Pour the batter in a pouring measuring cup with a spout, or any other type of container with a spout (this makes it easier to pour the batter into the paper baking cups). Fill the baking cups just a bit more than ½ full.
  • Bake at 350 F. for 22 to 25 minutes or until a toothpick comes out clean when inserted in the middle of a cupcake.  Let cool before adding the frosting.

For the Frosting:

  • Melt the butter. Stir in the cocoa and vanilla. Alternately add the powdered sugar and milk, beating on medium speed until the frosting is at a spreading consistency. If the frosting is not creamy, add a slight bit more milk and mix with a mixer.  Frost the cupcakes.
  • Gently remove the Goblins and Scary Trees from the wax paper and gently stick them into the frosting on top of each cupcake.
  • *Cupcake and frosting recipes adapted from Hershey’s “Perfectly Chocolate” Chocolate Cake and Frosting




  1. Make the candy goblins and scary trees first and let chill while making, baking and cooling the cupcakes.
  2. The frosting can be made while the cupcakes are cooling.

For the Goblins and Scary Trees:

  1. Make these one at a time so that the chocolate candy coating is soft enough for the Tootsie Roll goblin face and eyeballs to stick.
  2. When making the trees, try to add the chocolate on the wax paper on the thick side so when you remove them, the branches and the trunk won't break off.
  3. Make one tree at a time so the chocolate is soft enough for the eyeballs to stick.

For the Cupcakes:

  1. Before mixing the ingredients with a hand mixer, use a large spoon to stir all of the ingredients together a few times so that the flour and cocoa powder don’t create a huge dust storm in your kitchen when the mixer is used.
  2. An easy way to heat the water for the cupcake batter is in a microwave proof mug in the microwave.
  3. To prevent the cupcake batter from making a mess around the cupcake liners, use a pouring measuring cup to pour the batter into the paper baking cups.
  4. For this recipe, I have the best luck when I fill the batter half full in the paper cups so the top surface of each cupcake is a fairly level surface for the frosting.

For the Frosting:

  1. If the frosting isn't quite creamy enough, add a slight bit more milk and mix with a hand mixer.

Decorating the Cupcakes:

  1. Try to limit how much the chocolate goblins and trees are handled to prevent them from getting soft or melting from the warmth of your fingers.