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Peppermint Whoopie Pies for the Holidays

While my mom knows her way around a Chocolate Chip Cheesecake, my dad has always been the baker. And around Christmas time, my dad would make cookies.  I *think* he still does it, but it’s been a year or two since I’ve been home around Christmas and able to check the freezer, where he would store them. Because you know what taste better than an M&M cookie? A frozen M&M cookie! Trust me!

But since I’m not getting home this year around Christmas time, I thought it would be special to make cookies and tell my kids all about how Pop likes to make cookies too, especially at Christmas. Now my dad has made all kinds of cookies over the years, but the cookies that make me think of him the most are whoopie pies.

Whoopie pies are cookies with Amish roots, and are traditionally two chocolate, cake-like cookies sandwiched together with a cream filling. Occasionally you’ll see pumpkin and oatmeal whoopie pies too, but as a little nod to my dad – and my PA roots – I decided to take the whoopie pie and make a peppermint version!

Check out the rest of the yummy holiday cookies in the 2017 Holiday Cookie Swap!

Snowballs from Samantha at Carter's Cozy Nest
Paleo Chocolate Chip cookies from Mia at Mia Sutton Blog
Snickerdoodles from Lisa at Retro Housewife Goes Green
German Chocolate Cake Cookies from Abby at Winstead Wandering
Sugar Cookies from Lindsay at Pursuit of Pink
Vanillekipferl (Vanilla Almond Crescent Cookies) from Sandra at The In Between Is Mine
Gluten-free Chocolate Chip Cookies from Ashley at Happy. Pretty. Sweet.
Cloud Snickerdoodles from Savannah at The Savvy Plate
Peanut Butter Dreams Dog Treats from Beth at Daily Dog Tag
Grandma Hermits by Lecy at A Simpler Grace

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Peppermint Whoopie Pie Cookies

A holiday twist on a classic Amish cookie

Course Dessert
Prep Time 10 minutes
Cook Time 15 minutes
Total Time 1 hour

Ingredients

Chocolate Cookie

  • 2 cups flour
  • 1/4 cup unsweetened cocoa powder
  • 1 tsp baking powder
  • 1 tsp baking soda
  • 1 tsp salt
  • 1 cup packed brown sugar
  • 1 tsp vanilla extract
  • 1 cup whole milk
  • 1/2 cup shortening
  • 1 egg

Peppermint Cream Filling

  • 3 tbsp flour
  • dash salt
  • 1 cup milk
  • 3/4 cup shortening
  • 1-1/2 cups powdered sugar
  • 1 tsp vanilla extract
  • 5 drops Peppermint Essential Oil You could use Peppermint Extract as well - about 1 tsp or to taste

Instructions

Chocolate Cookies

  1. Pre-heat your oven to 350 degrees. Arrange a baking sheet liner or parchment paper on your baking sheet.

  2. Combine the flour, cocoa powder, baking powder, baking soda and salt.

    In a separate small bowl, combine the milk and vanilla extract. Set both aside.

  3. In the bowl of your stand mixer with the paddle attachment, cream together the sugar, shortening and egg. Slowly add in the dry ingredients and the milk mixture, alternating back and forth between the two, beating until the batter is well combined and smooth.

  4. Scoop the batter out into mounds on your prepared baking sheets, using a scant 1/4 cup for each mound and making sure to leave a couple inches in-between. Smooth or round out the mounds, making them as symmetrical as possible.

  5. Bake for 15 minutes. The cakes should be slightly firm to the touch when done. Remove them from the oven and allow the cakes to cool on their baking sheets for 5 minutes. Then transfer the cakes to a wire rack to cool completely.

Peppermint Cream Filling

  1. In a saucepan, combine flour and salt. Gradually whisk in milk until smooth; cook and stir over medium-high heat until thick, 5-7 minutes. You're looking for 'thicker than gravy but not ball-forming'

  2. Remove from heat. Cover and refrigerate until completely cool.

  3. In a mixing bowl, cream shortening, sugar, vanilla, and peppermint oil. Add chilled milk mixture; beat for 7 minutes or until fluffy.

    *A lot of time my dad would add a couple spoonfuls of marshmallow cream to the filling. I didn't when I made these because I didn't have it, but if you wanted to add it, just cut back on the powdered sugar and throw in a few spoonfuls of marshmallow cream! 

Making the Cookies

  1. Pair each cookies with a similar size cookie and spoon the cream filling onto the flat side of the cookie. Top the dollop of cream with the other cookie, and press down to push the cream to the edges.

  2. Roll the cookie in crushed candy cane for an added touch!

    You can also add a bit of crushed candy cane inside the cookie for a bit of crunch. 

    NOTE: Don't add the crushed candy cane until you're ready to serve. 

  3. To store, wrap each cookie individually in plastic wrap and store in the refrigerator. 

Recipe Notes

I used the recipe from The Floating Kitchen for the cookie part and slightly adapted the recipe from Taste of Home to make the cream filling - which is a closer representation of how my dad used to make the cookies and how I remember them. 

 

 

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