Preheat the oven to 350 degrees F. Line a baking sheet with a silicone mat or parchment paper.
Mix together the flour, baking powder, baking soda, salt and spices together. Whisk lightly to remove clumps.
In a separate bowl, mix together the remaining pumpkin cake ingredients until well combined. Add the wet ingredients to the flour mixture and mix until no lumps are present.
Scoop out two tablespoons of the batter and place on a baking sheet. Flatten. You should be able to fit about 9 large whoopie pies or 14 smaller ones on a baking sheet. Use a finger moistened with water to smooth out the tops of the pies. Alternatively, you may pipe out the pies using a plain tip.
Bake for about 14 - 18 minutes or until light and springy (my oven runs very hot and I found that the original minimum of 12 minutes to still be not nearly enough time). Take out and allow to cool completely.
While the cakes bake, make the ganache. Over a double boiler, add the chocolate and pepper. Mix together as the chocolate melts. In a seperate bowl, add the bourbon to the heavy cream and stir. Slowly add the bourbon mixture to the chocolate mixture. (Note: warmed heavy cream mixes better and creates a better consistency than chilled or room temperature cream). Set aside to cool to room temperature. Store in the refrigerator to firm slightly - about 20 mins.
Make the caramel drizzle.
Using a pastry brush, brush the flattened sides of the whoopie pies with the caramel twice. You can also dip the pies in the caramel if you want more of a caramel flavor.
Scoop a generous amount of the ganache on half of the whoopie pie cakes, then gently place the remaining whoopie pies on top of the ganache-covered halves. Serve immediately, or keep in an air tight container for up to three days.
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