Mint Filled Dark Chocolate Whoopie Pies

Whoopie Pies made with dark chocolate cookies and a soft minted filling.

There were inflamed protests from my family when I announced what my current recipe conquest-in-progress was.

Mint!?

No!

You’ll ruin them!

My family consists largely of strongly opinionated anti- mint/chocolate advocates.  I understand, I used to be one of them, but since marrying someone who loves the combination (thanks for making me try my first Thin Mint ever, Zach) I’ve definitely warmed to the flavor.

Whoopie Pies (or “Gobs”, as I’ve always known them to be called) are a very traditional dessert around here (we live not far at all from Amish Country) with a very classic taste to them.  To alter that taste was, evidently, blasphemous.

But I wanted to try something different.  I’ve been eating traditional gobs for years, easily putting away at least a neat half-dozen at any family event, and I have a scarcely opened bottle of peppermint extract that’s been rapping on the inside of my cabinet door, nagging me to find another use for it.

I started with a recipe that’s been in the family for a long time, but I decided on some key alterations.  The original recipe is fairly time-consuming and the original cookies have a very subtle, almost sour tang to them which would not have paired well with mint.  I tried to make the recipe a bit less time-consuming, and I wanted the cookies to be distinctly chocolaty.    Gobs are traditionally made with shortening and not butter, but I wanted something richer and darker, especially to complement the mint, and so butter was used here (though I did retain a portion of shortening in the filling).

The alterations were a success (my family was conveniently away at the beach when I made them, so I wasn’t able to procure their opinions) but the cookies turned out soft but stable enough to sandwich a substantial amount of mint filling, the entire dessert is sweet but not too sweet (nor too minty), a perfectly complementary play of mint and chocolate.

Unfortunately, evidently, I struggle greatly with properly capturing the pale green color that I used for the filling on camera, so these Gobs will probably be re-made and re-shot at some point in the near future (a great excuse to make them again, at least).

Mint Filled Dark Chocolate Whoopie Pies

5 from 2 votes

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Author: Sam Merritt

Ingredients

Cookies

• 1 cup granulated sugar
• 1/2 cup butter softened, 1 stick
• 1 large egg
• 1/2 tsp vanilla extract
• 2 cups all-purpose flour
• 1/3 cup Dark cocoa powder (regular cocoa powder would also work but the cookies will be lighter and have less of a dark chocolate taste)
• 1 tsp baking powder
• 1/2 tsp baking soda
• 1/2 tsp salt
• 1 cup milk

Mint Filling

• 1/2 cup butter softened, 1 stick
• 1/4 cup shortening
• 1 1/2 tsp peppermint extract (not "mint" extract which is a spearmint/peppermint combination)
• 4 cups powdered sugar
• 1/4 cup heavy cream
• 4-5 drops green food coloring optional
• 1 1/2 cup semisweet chocolate chips I used a combination of mini and regular-sized

Instructions

Cookies

• Preheat oven to 450F and line cookie sheet with parchment paper.
• In stand mixer (or in large bowl using hand mixer) beat together sugar and butter.
• Beat in egg until well-combined, and then stir in vanilla extract.
• In separate bowl, combine flour, cocoa powder, baking powder, baking soda and salt.
• Measure out milk and set aside.
• Starting with flour-mixture, gradually stir flour mixture and milk into batter, alternating (add about 1/5 of dry mix, as soon as ingredients are combined stir in approximately 1/5 of the milk, and repeat until all ingredients are combined). Batter will be fairly runny.
• Drop batter by 1-1 1/2" spoonfuls onto prepared cookie sheet, spacing at least 1 1/2" apart.
• Bake 5 minutes, remove from oven and allow to cool completely on cookie sheets before filing.

Filling

• In stand mixer (or in large bowl using hand mixer), cream together butter and shortening Stir in peppermint extract.
• Gradually add in powdered sugar, pausing occasionally to scrape down the sides of the bowl to ensure all ingredients are well-combined.
• Stir in heavy cream and beat on high for 1 minute.
• Stir in food coloring until desired color is attained and color is evenly distributed.
• Stir in chocolate chips.
• Pair together cooled cookies by similar size. Spread frosting over the bottom of a cookie and sandwich with another cookie (i used about 1 1/2 - 2 Tbsp filling per whoopie pie). Repeat until all cookies/filling are used and serve.

Tried this recipe?Mention @SugarSpun_Sam or tag #sugarspunrun!

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