Dark Chocolate Candy Cane Whoopie Pies

Dark Chocolate Peppermint Whoopie Pies

The Story:

I grew up with a big white cookie jar sitting on the kitchen counter.  Was it filled with freshly baked cookies and treats? Piled high with brownies? Or candy bars and chocolates?  Nope.  This was a different kind of cookie jar.  It was the place where things sort of got left behind. Old suckers from the doctor, gross-flavored cough drops and at the bottom there were always candy  canes.  Crushed and broken and missing their Christmas charm.

So today I’m bringing the magic back to broken candy canes (the ones I used here were new and not old)!  Do you hang you canes on the tree?  Suck on them while you decorate?  Well now you have one more reason to love these shepherd crook candies![end-story]

Dark Chocolate Candy Cane Whoopie Pies

Yield: 20-30 cookies, 10-15 whoopie pies

Dark Chocolate Candy Cane Whoopie Pies


Dark Chocolate Cookies:
Pillsbury® Dark Chocolate Premium Cake Mix
2 eggs
2 Tbsp. brown sugar
1/2 C. oil
Peppermint Cream Cheese Filling:
8 oz. cream cheese
1/4 C. butter, softened
1 tsp. peppermint extract
2 tsp. vanilla extract
2-3 C. powered sugar
6-8 candy canes, crushed


1. Preheat oven to 350 degrees.
2. In a large bowl, combine cake mix, eggs, brown sugar and oil until smooth. Dough will be thick.
3. Make small dough balls and place on cookies sheets. gently press down on each dough ball to flatten a little (cake mix cookies bake really tall unless you flatten them out.)
4. Bake for 6-10 minutes depending on how large each dough ball is (walnut-sized to golf ball-sized)
5. Let cool.
6. Cream cheese filling: Beat cream cheese and butter. Add vanilla and peppermint extract and slowly add in powdered sugar until you reach your desired consistency.
7. Frost the bottoms on half of your cookies. Then use an unfrosted cookie to "sandwich" your filling in between the two cookies.
8. Roll the edges in a bowl of crushed candy canes. (Crush your candy canes in a blender, it's really fast that way!)
9. Enjoy! (You can place in a tupperware in the fridge until ready to serve! They taste great chilled!)

Loved this Dark Chocolate mix!  It works with any of my cake mix recipes that calls for Devil’s Food Cake Mix.  You can also use the Chocolate Peppermint Cookie Mix if you want and even easier way to make this recipe work! 

Pillsbury dark chocolate cake mix

Love my cookie scoop!  It’s a great stocking stuffer for any baker… just saying 🙂  

best cookie dough scoop

Remember, cake mix cookies need to be flattened down a bit so they don’t bake up too tall!  I made my cookie really big, but you can make them half the size and they will be adorable! 

cake mix cookies

These are really easy to pack in a little box and give to neighbors or send in your kid’s lunch box! 

Dark Chocolate Peppermint Whoopies

Candy cane season has arrived!

Candy Cane Whoopie Pies

 ©/® The J.M. Smucker Company. Pillsbury is a trademark of The Pillsbury Company, LLC, used under license. Your Cup of Cake was compensated for this post.

17 thoughts on “Dark Chocolate Candy Cane Whoopie Pies

  1. 1
    Genia says:

    My youngest has started “stalking” your website! I believe he has a bit of a crush on you. hahaha Anyway, since he hasn’t been successful at getting me to make any of your whoopie pies, he’s started breaking the bottom off on his cupcakes and putting that piece of cake on top of the frosting and then eating it.

  2. 2
    Tamara says:

    I can identify exactly with your cookie jar story, except I always used the extra canister (the one intended for coffee or tea). What brand is your cookie scoop and where can I get one?

    • 2.1

      I liked to it where I mentioned it! Click the “my cookie scoop” part of the sentence above the scoop photo! I like the black or purple or cookies, blue if you want big cookies! And I like blue and yellow for cupcakes!

  3. 3
    Chelsey says:

    What brand of peppermint extract do you use? The kind I have tastes really bad, really fake tasting. These look yummy!

    • 3.1

      Mm… I use different kinds but I always make sure it’s not imitation or anything like that. I know Trader Joes has one in stores right now! That’s probably the best for the best price!

  4. 4
    Pennie says:

    Hey, Lizzy! Just wondering, but do you think the peppermint cream cheese filling for these would work for the frosting on a chocolate cupcake?

  5. 5
    Mallory says:

    If I made these two nights before they were going to be served, but didn’t put the filling in until the day they were served, do you think they would hold up okay?

  6. 6
    Patti says:

    Thanks for the recipe, Lizzy! I just received a whoopie pie pan ~ would that work with this recipe?

  7. 7

    Hi! Just wanted to say that you are my number 1 role model! I am mormon too, currently a beehive. Also I love baking too! I started my own buissiness in the summer, and I have been loving it! Then, I started to think nobody really wanted to eat my stuff and just ate it to be nice. This was a downpoint for me until a came across your cookbook at The Deseret Book Store! It really just kinda lifted me up with all those amazing recipes. Let me just say that your book is the best I have ever seen! Now my buissiness, The Goodies In Life, is doing fantastic and quite a few orders are coming in. Anyway, cant wait till your next book comes out, wink wink.
    With love,
    Karina Houser

    • 7.1

      Oh thank you so much! You are too sweet! I have a product out that just got shipped to the stores (hopefully you’ll se it aroun) and another big book coming out in the Spring. Come find me at a book signing!

  8. 8
    Clayne Leitner says:

    Do you think I would be able to make one large cookie with this mix. Sort of like they make those large chocolate chip cookies?
    If so how long would I bake it? This would be for my wife’s 70th birthday. I just found this box in the pantry.

    • 8.1

      Yes you can! Cooking time… hmm… It just depends if you want a soft or a crunchier cookie ALSO depends on how big you want it though! I would say probably 15-20 minutes but that really will depend on how thick it is! Make sure to make a big “disk” out of the dough and not just make one HUGE dough ball 🙂

      • Clayne Leitner says:

        I just finished (with my wife’s help), and it came out great. We mixed 1/3 cup of mini-chocolate chips into the dough. Put dough in a 9 1/2 x 13 pan with 1/2 inch sides and spread completely. Used parchment paper on bottom and sprayed with Pam. Baked for 15 minutes and cooled. I’m going to frost with vanilla icing from the store laced with peppermint extract then sprinkle with the peppermint chips that came with the mix.

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