Chocolate Crinkle Whoopie Pies with Peppermint Buttercream Filling

Chocolate Crinkle Whoopie Pies with Peppermint Buttercream Filling

I have had this chocolate crinkle cookie recipe for years and it's always a big hit with my family and friends...and Santa too. But I wanted to create something new from it and add some more fun and flavor. So, I decided to add a peppermint buttercream filling and make these into a sandwich cookie/whoppie pie!

The below includes the cookie recipe and the filling. And if you aren't a filling fan, you can still just make the regular cookies: chocolate crinkle cookie. They are both amazing. Trust me, if you leave these for Santa, he will leave you all the presents you want.

Cake mix cookies are so easy to make and always a good recipe to have up your sleeve. And now you can make them plain or you can fill them! Giving your at least two options for cookies. These are great cookies for the holidays. Whether you’re making them for a party or making them for the perfect holiday cookie box. They are an amazing Christmas cookie.

So, whether you are gifting to friends, neighbors, Santa, or yourself, you’ll definitely be impressing all.

This recipe only makes 14 sandwich cookies. You can easily double this recipe. I usually still make my batches separately and chill them together.

Table of Contents

Chocolate Crinkle Cookies Cake Mix

Using cake mix takes the stress out of finding/having the right ingredients, but is also a great time saver! And for those non-bakers, this recipe is just a few steps easier. You’re still making something unique and different, so don’t think that this is cheating or not baking from scratch, you still are!

I used to make these and my gooey butter cake cookies from scratch, however, I know that not everyone carries these ingredients in their houses, so I've posted recipes using cake mixes! Of course, you can simply replace those mixes with your own favorite dry cake mix ingredients. Which means these are easy to make gluten free as well.

How to Customize Your Cookies

These can be jazzed up in a bunch of different ways. A few different things I like to do are:

1. The basic way, just the basic cookie.
2. You could also do this with other cake batter flavors of course and powdered sugar. An easy way to customize the flavors for these is to simply use a different flavor cake mix. It’s seriously that easy. You can use vanilla, red velvet, whatever floats your boat. Some will spread more than others just by their other ingredients. But, it’s fun to play with them and see what you can make.

3. For birthdays and celebrations, coat with powdered sugar and sprinkles. You probably want a type of wax coated sprinkles so they bake okay. Something like a jimmie or even a quin.
4. I made a sugar-free version for my dad with a sugar-free cake batter. The powdered sugar part is a little more difficult, so I usually just use less since most “sugar-free powdered sugar” won’t bake on your cookie.
5. Grind peppermint sticks and powdered sugar together for a Christmas version!

How do Cookies Crinkle?

A crinkle cookie is usually a drop cookie or “rolled” cookie. It’s one you scoop, roll, and toss into a sugar. Whether granulated or powdered. This will make the outside of the cookie bake first, and dries it out. Which then as the middle of the cookie bakes and expands, it separates the outside of the cookie, creating that iconic crinkled outside.

How do you prepare a baking sheet?

Most recipes call for a step that is to “prepare your baking sheet” while your oven preheats. This is simply laying down a cut piece of parchment paper or a silicone baking mat. I almost always use parchment. You can reuse it for the next batch you put in the oven and it helps for a crispy bottom of your cookie. Silicone can sometime not create the desired texture you want on the bottom of a cookie.

You can usually also substitute foil in as well, however, the chemicals in foil aren’t something I like to mess with very much. However, if I do use foil I like to use If You Care Recycled Aluminum Foil. I also prefer their parchment paper as it’s recycled. I get mine from Grove Collaborative.

And, of course, you can bake without anything, but it might cause the cookies to stick. And greasing a baking sheet for cookies isn’t advisable as then your cookies will have a greasy or soggy bottom. And no one likes that.

Best Neutral Oil for Baking

Often, you’ll see baking recipes calling for a neutral oil. A neutral oil when it comes to baking would be an oil like grape seed (my personal favorite to bake with), canola, or vegetable oil. Different oils could leave a flavor that would be unwanted in your bake, such as olive oil or peanut oil. They can be used if you don’t have the others, but they can also leave a taste behind, many people have nut allergies, and they also have different heat points. Which doesn’t always affect a bake, but can.

Most often you can replace a neutral oil with melted butter, but the recipe might vary, so be cautious.

Chocolate Crinkle Cookie Sandwich Recipe

Cookie Ingredients

• chocolate cake mix
• eggs
• oil or melted butter
• vanilla extract

How to Make Chocolate Crinkle Cookies

1. Combine the wet ingredients until thoroughly mixed. Then slowly add in your chocolate cake mix.
2. Chill dough in refrigerator for at least 30 minutes to 8 hours.
3. When you're ready to bake, preheat your oven to 350° F.
4. Place your powdered sugar into a separate bowl.
5. Scoop a spoonful of dough into your hands and roll into a ball. Drop a few of the dough balls into the powdered sugar and toss to coat.
6. Place the dough balls onto an un-greased cookie sheet and bake for 10-12 minutes.
7. Cool.

Cookie Sandwich Filling Recipe

Ingredients

• powdered sugar
• unsalted butter, softened at room temperature
• whole milk (or heavy cream)
• peppermint extract
• powdered sugar, sifted 1-2 times
• peppermint crushed candies (my favorite comes from World Market)
• Optional extra peppermint candies powdered for outside of cookies optional

How to Make Peppermint Buttercream

1. Using your mixer and the paddle attachment, whip the butter for 8 minutes on medium/low speed. The butter will become very creamy!
2. Add milk and peppermint extract. Stir for 30-60 seconds until incorporated.
3. Add peppermint extract, taste to see if you would like a little extra flavoring (I keep mine lower as I add in the candies later).
4. Add the powdered sugar in 3 batches. The frosting should become very light and fluffy.
5. Add in crushed candies until mixed thoroughly.
6. Assemble the cooled cookies with frosting. I use a piping bag for flair, but feel free to just scoop with a spoon. You can also add more powdered sugar and/or powdered sugar to completed cookies.

How to Assemble Whoopie Pies

1. Pipe or scoop filling onto 1 cookie, then sandwich together with another cookie.
2. Enjoy!

FAQ about Chocolate Crinkle Whoopie Pies

Video - How to Fill Sandwich Cookies

Other Cookie Recipes to Try

• Gooey Butter Cake Cookies
• Chocolate Crinkle Cookie
• Holiday Cookie Box
• Molasses Cookies
• Perfect Chocolate Chip Cookies
• Graham Cracker Crumble Soft Butter Cookies
• Double Chocolate Chunk Cookies
• Snickerdoodles
• Oatmeal Cookies
• Lucky Charms Cookies

Love this Recipe?

Did you make this recipe and just love it? Awesome! If you have a quick minute and could leave a star rating and comment below, I would appreciate the support and knowing your feedback! And if you’re over on Instagram, be sure to tag me in your photos!