Chocolate Pumpkin Whoopie Pies

I have a confession for you all… I’ve never made a whoopie pie, well, until a few days ago. I’m not sure how I’ve made it through all of these “culinary” adventures without doing so. I have however, helped my mom make her famous mint “sandwich cookies,” which people mistakingly call whoopies, but for me, a whoppie pie is cake-like with a soft frosted center. So lets count those mint ones out, deal? Well, like I said, I finally decided it was time to try my hand at making some. I love the idea of pumpkin and chocolate together, so I decided on these little pies. Yes they’re a bit funky looking, not exactly smooth and flawless like most traditional whoopies, but they definitely make up for that in taste! They’re soft and sweet and full of that pumpkin flavor that we all love so much… oh, and did I mention that there are mini chocolate chips in there too? Yep… they’re kind of perfect 🙂 Enjoy!

Chocolate Pumpkin Whoopie Pies
2 c. all-purpose flour
¾ c. unsweetened cocoa powder
1¼ c. sugar
8 tbsp. (1 stick) butter, room temperature
1 c. buttermilk, room temperature
1 egg
1½ tsp. baking soda
½ tsp. baking powder
¹⁄₈ tsp. salt
1 tsp. vanilla

Pumpkin Chocolate Chip Filling:
¾ c. powdered sugar
6 oz. cream cheese, room temperature
4 tbsp. (½ stick) butter, room temperature
¼ c. pumpkin puree
¼ tsp. pumpkin pie spice
¹⁄₈ tsp. salt
¼ tsp. vanilla
¼ c. mini semi-sweet chocolate chips

1. Preheat oven to 400 degrees. Line 2 baking sheets with parchment paper, set aside.
2. In the bowl of a stand mixer, beat together butter and sugar until light and fluffy (2-3 minutes). Add the egg, buttermilk and vanilla, mix until incorporated.
3. In a medium size bowl, whisk together flour, cocoa powder, baking soda, baking powder and salt. With mixing speed on low, gradually add the dry ingredients. Mix until just combined (the dough will look more like a batter- remember these are cake-like).
4. Remove bowl from stand place in refrigerator for 15 minutes. Once the dough has chilled, scoop 12 balls of dough (about the size of 2 tbsp.) onto the prepared cookie sheets. Place in oven and bake until the edges begin to set (approximately 8-9 minutes), be careful not to overbake. Remove from oven and let cool on sheets for 5 minutes before transferring to a wire rack to cool completely. Repeat the process with the remaining dough.
5. While the cookies are cooling, to prepare the filling, in the bowl of a stand mixer fitted with the whisk attachment, beat together cream cheese, butter and pumpkin. Add in pumpkin pie spice, salt and vanilla. With mixing speed on low, gradually add powdered sugar. Beat for 2-3 minutes until light and fluffy. Fold in mini chocolate chips (or roll edges in once they have been frosted).
6. Pipe filling onto the flat side of one cookie, then sandwhich. Continue until all of the cookies have been piped and sandwiched.
Adapted from Food Network Magazine, Whoopie Pumpkin Pies | Makes approximately 12 whoopie pies