Spiced Chocolate Pumpkin Whoopie Pies

posted on October 18, 2010

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I am SO excited that it’s fall: the cool weather, warm-colored leaves, sitting by the toasty fire, and LOTS AND LOTS of pumpkin! I cannot even begin to describe my love for the big, orange squash, buuuut I can show you:

Pumpkin and Black Bean Quesadillas

Quick Pumpkin Butter

Curried Pumpkin Lentil Soup

Pumpkin Shortbread

Pumpkin Banana Cream Pie

Throw-it-Together Pumpkin Soup

…and that’s only the stuff I’ve actually posted. I think it’s safe to say that I’m more than a little obsessed. Hence, when I saw these whoopie pies I absolutely HAD to try them. Plus, they are almost “too” perfect for Halloween; check out that black and orange combo (also note the adorable spooky cupcake liners 🙂 ).

I had never made whoopie pies before, and though I was a bit nervous, I had always wanted to give them a try. Honestly, I don’t know what I was worried about. They could not have been easier to make and I cannot wait to try my hand at some more fun flavor combinations (though it will, of course, be hard to top pumpkin).

These turned out absolutely fabulous! The cookies (cake?) turned out perfectly soft and pillowy, and the filling was all I had hoped it would be- spice-y (not spicy), pumpkin-y rich, and ultra creamy- a sweet, little package of fall in edible form!

I sent the whoopie pies to work with Mikey and he came home with empty tupperware- a definite good sign! Apparently they were quite a hit :D.

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Spiced Chocolate Pumpkin Whoopie Pies

Yield: makes roughly 35 (fairly large) whoopie pies

Ingredients:

for the cookies:

3 and 1/2 cups all-purpose flour
1 and 1/2 cups unsweetened cocoa powder(I used Dutch-processed)
1 tbsp baking soda
1 tsp sea salt
2 tbsp unsalted butter, at room temperature
1/2 cup vegetable shortening
1 cup granulated sugar
2 lage eggs
2 cups whole milk
2 tsp pure vanilla extract (not so funny story: I thought the vanilla was my Diet Coke while baking and I took a MASSIVE swig. I DO NOT recommend it.)

for the filling:

8 oz cream cheese, at room temperature (I used Neufchatel which has 1/3 less fat)
2 sticks (1 cup) unsalted butter, at room temperature
1 cup confectioners' sugar
3/4 cup canned pure pumpkin
grated cinnamon, to taste
freshly grated nutmeg, to taste (I used close to maybe 3/4 tbsp of each- possibly more- I like mine quite fragrant.)

Directions:

for the cookies:

Preheat oven to 375 degrees. Line baking sheets with silicone baking mats or parchment paper; set aside.
In a medium bowl, combine the flour, cocoa powder, baking soda, and salt; set aside.
In the bowl of an electric mixer fitted with the paddle attachment, mix together the butter, shortening, and sugars for about 3 minutes until creamy and smooth. Add in the eggs and vanilla and mix for around 2 more minutes.
Alternately add in the flour mixture and milk on low speed, beginning and ending with the flour.
Scoop dough 2-inches apart onto prepared baking sheet in about a tablespoon-sized mound (I used a small cookie scoop.). Bake for 12 minutes or until the cookies spring back when lightly touched.
Allow cookies to cool on baking sheet for 5-10minutes before transferring to a wire rack to cool completely.

for the filling:

In a medium bowl, beat together the cream cheese, butter and confectioners' sugar until smooth.
Add in the pumpkin and spices and mix until smooth, scraping down the bowl as necessary.

to assemble:

Spoon a tablespoon-sized amount of filling onto the flat side of one of the cookies and top with another cookie. Repeat the sandwich-making process with the rest of the cookies/filling.

recipe slightly adapted from here