Halloween Whoopie Pies

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These festive Halloween Whoopie Pies are a spooky and sweet treat perfect for Halloween! Rich, chocolate cake cookies sandwich a smooth and fluffy orange colored vanilla buttercream for the perfect balance of chocolate and creamy sweetness.

It’s almost Halloween and that means I’ve been busy in the kitchen working on all the festive holiday treats.   Halloween is one of my favorite holidays so I usually start baking sweets in August to get ready. 

We’ve had a lot of chocolate milk lately and we rarely finish it so I’ve been attempting to find baked good recipes to use the remaining milk.   Since Halloween is coming soon I wanted to find a new recipe for the occasion!

I have plenty of Halloween desserts already on my website.  My Easy Spider Cupcakes have been a recent favorite. When I want a show stopping dessert I go for Candy Corn Layered Cakes. If I’m baking for kids I usually go with Caramel Swirl Silly Pumpkin Cupcakes.

I found a recipe for Halloween Whoopie Pies that used chocolate milk.  Can you believe I’ve never made a whoopie pie before?   They are so popular in my area yet I’ve never made one until now.

What is a Whoopie Pie?

A whoopie pie is a classic American dessert made of two soft, cake like cookies sandwiched together with a creamy filling. The cookies are typically round and domed, with a texture somewhere between cake and cookie.

So there are two main parts to the whoopie pie.  The first is the cake like cookie that holds the filling. In this case it’s a moist and delicious chocolate cookie. 

Why are these chocolate whoopie pies the best?

They are the best because they are made with chocolate milk!  The chocolate milk adds a rich, chocolate flavor that isn’t overly sweet.  It also makes the cookies moist.

The second part of the whoopie pie is the filling.  You can make a traditional buttercream filling, a marshmallow cream filling, or a flavored filling.  I chose to go with a traditional vanilla buttercream to pair with the chocolate cookies. 

I did use food coloring to make the buttercream orange in order to have orange and black whoopie pies. I always use Americolor Gel Food Coloring when coloring my frosting and icing because you only need a few drops to get a true color. 

Then I put little eyes on the whoopie pies so they looked like monsters.  I simply used some of the leftover frosting and put white dots on the cookies with a dot of black frosting in the center.  If you don’t want to do that you can use candy eyes. 

Ingredients:

• all purpose flour
• unsweetened cocoa powder (you can use Dutch processed cocoa if you would like)
• baking soda
• salt
• salted butter (you can use unsalted but I think the salt helps cut through the sweetness)
• brown sugar (I use light but you can use dark)
• eggs
• prepared coffee (optional but makes the chocolate flavor pop)
• vanilla extract
• chocolate milk

To make the chocolate sandwich cookies preheat the oven to 350 degrees.  In a large bowl whisk together the flour, cocoa powder, baking soda, and salt.  Set aside. 

In another large bowl cream together the butter and sugar.  Add in the eggs, prepared coffee, and vanilla extract and mix well to combine. Add half of the flour mixture to the butter mixture and mix well.  Stir in the chocolate milk until well combined.  Add the remaining flour mixture and mix until just combined. 

Using a 4 Tablespoon cookie scoop, scoop the batter onto a baking sheet allowing at least 3 inches in between the dough scoops.  Bake for 10-12 minutes or until the cookie cakes spring back when you touch them. Cool on the baking sheet for 5 minutes before removing to a cooling rack to cool completely. 

Fill the cookies with the buttercream frosting and top with the frosting eyes. 

These whoopie pies were so fun to make!   I enjoyed making the orange buttercream to fill the chocolate cookies with.  I also liked putting the eyes on top. 

The filling to cake ratio was perfect.  The cookie cakes are sweet but not overly so and have a rich chocolate flavor.  The vanilla buttercream is smooth and velvety. 

How do you store the whoopie pies?

Since the cookie cakes are hard to stack I’ve found that wrapping each whoopie pie in plastic wrap the placing them in an air tight container for up to 5 days works the best. 

The best part about these whoopie pies is that you can customize them for any occasion.  Fill with red or green frosting for Christmas, with blue or pink filling for a gender reveal, or pastel colors for Easter!

Halloween Whoopie Pies

Chocolate cookie cakes sandwich fluffy vanilla buttercream frosting.

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Prep Time: 40 minutes minutes

Cook Time: 12 minutes minutes

Total Time: 52 minutes minutes

Servings: 12 whoopie pies

Author: Hezzi-D

Equipment

• 2 mixing bowls
• 1 Large cookie scoop
• 1 cookie sheet
• 1 piping bag
• 1 Wire Cooling Rack
• 1 hand mixer

Ingredients

For the Whoopie Pies:

• 4 cups all purpose flour
• 1 1/3 cups unsweetened cocoa powder
• 2 teaspoons baking soda
• 1 teaspoon salt
• 1 cup salted butter softened
• 2 cups light brown sugar packed
• 2 eggs
• 3 Tablespoons prepared coffee
• 1 teaspoon vanilla extract
• 2 cups chocolate milk

For the Buttercream Frosting:

• 1 cup salted butter softened
• 4 cups powdered sugar
• 2-3 Tablespoons milk
• orange food coloring
• black food coloring

Instructions

• To make the chocolate cookies preheat the oven to 350 degrees.
• In a large bowl combine the flour, cocoa powder, baking soda, and salt. Mix well to combine.
• In another large bowl cream together the butter and sugar. Add in the eggs and mix well.
• Stir in the vanilla and coffee and mix well.
• Add half the flour mixture to the butter mixture and mix well to combine.
• Slowly add the chocolate milk, stirring frequently, until well combined.
• Add the remaining flour mixture and mix until just combined.
• Using a 4 Tablespoon cookie scoop, scoop the chocolate dough onto a cookie sheet leaving 3 inches between each scoop.
• Bake for 10-12 minutes or until the cookie cakes spring back when touched. All to cool on the baking sheet for 5 minutes before removing to a wire rack to cool completely.
• To make the buttercream frosting place the butter in a large bowl and use a mixer on medium speed to beat until smooth. Add the powdered sugar a cup at a time, mixing on medium speed after each addition.
• Add the milk and vanilla and mix on medium speed for 1 minute. Increase to high speed and beat an additional minute.
• Remove 1/3 cup of frosting from the bowl. Dye the remaining frosting orange.
• Turn 12 cookies flat side up. Pipe or spoon frosting all over the cookie, top with another cookie so that you have 12 whoopie pies.
• Use the remaining white frosting to make 2 eyes on each cookie. Dye any remaining frosting black and place a small dot in the center of each eye.

Notes

Recipe adapted from Melanie Makes