Halloween Brownie Roll Out Cookie Sandwiches

Happy almost Halloween everyone!  I feel like the fall holidays are always overshadowed by Christmas every year. Halloween and Thanksgiving have yet to pass and Christmas music is already being played and all the stores have their winter holidays sections ready to go. Don’t get me wrong, all that shiny stuff does make me happy, but we gotta take care of the darker side first.

Yes my friends come to the dark side, we have cookies! (Oh my goodness I am sorry I had to. The entire time I was making these I kept thinking of that shirt.) But seriously, these arn’t your typical cut out sugar cookies – they’re chocolate! Although they are not as chocolatey as I had imagined they would be so it’s a good thing there’s frosting sandwiched in between. Frosting makes everything better, especially when it is cream cheese (at least I think so).

More Halloween ideas:


Makes 18 cookie sandwiches, or 3 dozen cookies



3 cups all-purpose flour

2/3 cup cocoa powder

1/2 tsp salt

1/2 tsp baking powder

1 cup butter, softened

1-1/2 cups sugar

2 large eggs

1-1/2 tsp vanilla extract


6 oz. reduced fat cream cheese, at room temperature

4 Tbsp unsalted butter, at room temperature

1/2 cup confectioner’s sugar

1 Tbsp milk

1/2 tsp vanilla extract

Food coloring


  1. Mix together the flour, cocoa, salt and baking powder in bowl and set aside.
  2. In a large bowl, cream butter, sugar together. Followed by the eggs and vanilla.
  3. Gradually add the dry flour mixture into the wet mixture. Wrap in plastic and chill for at least one hour.
  4. Preheat oven to 350 degrees.
  5. Roll out the cookie dough on floured counter to 1/4 inch thick. Use cookie dough cutters to cut into desired shapes: cut out cookies using pumpkin or skull outline side of cutter. Then, use the other side of the cutter to create skull or pumpkin faces in half of the cookies.
  6. Bake on a lined baking sheet for 10 minutes or until the edges are firm and the centers are slightly soft and puffed. Transfer to a cooling rack.
  7. Meanwhile, make the filling: In a small bowl, whisk together the cream cheese, butter, confectioner’s sugar, milk and vanilla until smooth and fluffy. Add food coloring and mix thoroughly. Spread about 1 tablespoon filling on each non-face cookie and top with a cut-out cookie.

Source: Idea from Target’s Halloween double-sided cookie cutter set. Cookies discovered on Lovin’ From the Oven, originally from Smitten Kitchen. Frosting adapted slightly from Alton Brown on Food Network.


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