This isn’t really a “traditional” whoopie pie, because the sandwich part is less cake and more cookie, but it does have a decadent marshmallow/cinnamon buttercream center, so I’m calling it a whoopie pie. Feel free to call them anything you like – but one thing you’ll definitely call them is delicious.
Ingredients
Sandwich Cookie- 2 cups flour
- 2 t baking soda
- 1 t cinnamon
- ½ t ginger
- ¼ t nutmeg
- ¼ t allspice
- ¼ t ground cloves
- 1/8 t black pepper
- Pinch of salt
- ¾ cup butter, brought to room temperature
- ½ cup dark brown sugar
- 1 cup sugar, separated
- 1 egg
- ¼ cup molasses
Filling
- 1 cup butter, brought to room temperature
- 7 ounces (1 container) marshmallow fluff
- 3 t vanilla
- 1 t cinnamon
- Pinch of salt
- 3 ½ cups powdered sugar
Directions
In a medium bowl, add the flour, baking soda, cinnamon, ginger, nutmeg, allspice, cloves, black pepper and salt and whisk until everything is evenly distributed. Set the bowl to the side.Next, in a large bowl put the butter, brown sugar and ½ cup of the sugar and cream together until smooth.
Add in the egg and molasses and mix again until well incorporated.

Finally, get your bowl of dry ingredients and slowly add that to the wet ingredients, mixing the entire time until just combined.

Add the remaining ½ cup of sugar to a small bowl. Roll the dough into ping pong-sized balls and roll each one in the sugar.
Line baking sheets with parchment paper and place the balls of dough on them, six or eight to a sheet, depending how large you want your cookies to be. Press down lightly with the palm of your hand to flatten them a little.

Bake at 350 for about 8-10 minutes, or until the edges are slightly golden brown. Let them cool on the baking sheet for a couple minutes, then move them to a wire rack to cool completely.

Once the cookies are cool, you can start making the buttercream, which is pretty easy.
Cream the butter in a large bowl. Next, add the marshmallow fluff, vanilla, cinnamon and salt and mix until well combined. Finally, slowly add in the powdered sugar, mixing throughout until well combined.

Take a sheet of parchment paper and lay it on the counter. Get your cooled cookies and pair them off into approximately equal-sized pairs, flat side up.

Get your buttercream filling and either spread it or pipe it onto one of each pair of cookies. Take the other half and gently press down on the buttercream.

I would put these in the fridge for about an hour to let filling set, and then you’re good to go! They can be served cool or room temperature.
Making them the size I did resulted in about 30 delicious gingerbread whoopie pies! Your mileage may vary, depending on how large you make the cookies.
