Dark Chocolate Chip Holiday Mint Whoopie Pies

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Despite my large collection of cookie recipes on She Bakes Here, there is one type that I don’t make very often, and that is whoopie pies. The last time I tried to make them was back in 2011 during my first months of blogging. This was also when I was really into making healthy versions of everything, even if it didn’t always taste very good. One of my more common substitutions was full whole wheat flour in the place of regular all-purpose flour and in the end, without fail, the dough would always be dense, resulting in heavier cupcakes, cakes and cookies. I know I had good intentions with my first whoopie pie cookies (made for a bake sale no less….ugggh), but I knew that if I was to try making them again, I would have to ditch the healthy substitutions.

I’m not familiar with any bakeries in Toronto that sell whoopie pies, so making these cookies was definitely a treat. I’ve seen cookbooks dedicated solely to the different varieties that are out there, but seeing as how it’s the holiday season, I felt the need to further exhaust my favourite mint and chocolate flavour combination. Besides, who can turn down what essentially is a beautiful fluffy mountain of mint icing sandwiched between two soft, chocolate cake-like cookies. I’m not even a huge fan of chocolate cake and I’ve already proclaimed my undying love to these cookies.

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The recipe I adapted comes from Dulce Dough and you can tell from her cute little perfectly sized cookies that Jill used a whoopie pie pan. However, due to my dislike for owning single purpose kitchen gadgets, I forgo’ed the idea of purchasing of the pan and figured that if I prayed to the Baking Gods hard enough, maybe a few of my cookies would morph into the same shape. This way, it would at least give me a great excuse to munch on the misshapen ones while I took my photos.

In adapting her recipe, I had to add a bit more flour so that my cookies would keep their shape during the baking process while remaining cake-like and fluffy. Some other alterations I made were using Ghirardelli Natural Unsweetened Cocoa to amp up the chocolate intensity and a teaspoon of espresso powder to jack up the caffeine. (Actually, you won’t even notice the espresso in the cookies, I just like adding it to anything with chocolate). Finally, I threw in a 1/2 cup of dark chocolate chips to the batter just before I started scooping. There was no real reason to do this other than to feed my love of cake with chocolate chips nestled inside.

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The cookies did spread out a little more than I liked, but that seemed to have more to do with the size of the cookies themselves than anything else. I alternated somewhat between using a full tablespoon and a 1/2 tablespoon until I finally achieved the cookie size that I wanted. Next time I may even go smaller just to see if I can achieve a classic bite-sized whoopie pie.

As the cookies cooled, I whipped up a quick batch of mint icing and then played matchmaker, pairing up each cookie to their respectably sized suitors. The icing was piped to the bottom of half of the cookies and then topped with their partners. My original plan was to roll the edges of each cookie in a bowl of sprinkles to make them stick to the icing, but since the cookies were so soft, the sprinkles stuck to everything. In the end, I just held each cookie over the bowl and literally sprinkled them until I was satisfied and my fingers were stained a variety of colours. I may have also eaten one or three. Hey, it happens.

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Dark Chocolate Holiday Mint Whoopie Pies 30 cookies*

Total Time: 1 hour 15 minutes

Ingredients:

Cookies

  • 1/2 cup butter/margarine, softened
  • 1 cup brown sugar
  • 1 egg
  • 1 tsp vanilla extract
  • 3/4 cup almond milk
  • 1 tsp apple cider vinegar
  • 2 1/4 cups flour
  • 1/2 cup dark cocoa powder
  • 1 tsp espresso powder
  • 1 1/4 tsp baking soda
  • 1/4 tsp salt
  • 1/2 cup dark chocolate chips (optional)

Icing

  • 1/4 cup butter/margarine, soften
  • 2 cups powdered icing sugar
  • 1 tsp mint extract
  • 1 1/2 tbsp almond milk

Directions:

  1. Preheat oven to 350*F and prepare your baking sheets with parchment paper or baking liners.
  2. In a large bowl, cream together butter/margarine and brown sugar. Add the egg and vanilla extract and continuing mixing until smooth.
  3. In a small glass measuring cup, combine almond milk and apple cider vinegar. Set aside.
  4. In a separate bowl, whisk together flour, dark cocoa powder, espresso powder, baking soda and salt.
  5. Alternate adding the flour mixture and the almond/vinegar to the wet mixture and mix until combined.
  6. If adding chocolate chips, stir in with a wooden spoon.
  7. Drop the cookie dough in mounds 1/2 to 1 tablespoon in size on the prepared cookie sheets. Bake for 8 minutes until the tops of the cookie puffs up and springs back when lightly touched.
  8. Let cool on the baking sheet for a few minutes before transferring to wired rack to cool completely. Be careful when stacking the cookies as they may stick together and break.
  9. To making the icing, cream together butter/margarine and powdered icing sugar until crumbly. Add mint extract and almond milk and blend until smooth. Pipe icing onto the bottom of cookies and top with another cookie and serve.

*Amount will vary on the size of cookies

Cookie recipe adapted from Dulce Dough

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One Response to “Dark Chocolate Chip Holiday Mint Whoopie Pies”

  1. #
    1
    AJ — March 11, 2014 at 5:24 pm

    Hi Jessica, just found your blog and I love it (I live in Toronto too)! These really caught my eye because I grew up in Pennsylvania dutch country where whoopie pies were a regular treat (along with shoo-fly pie and other delicacies). They look so fun and festive, I will have to try a batch.

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