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Peppermint Whoopie Pies

Oh how I love the combination of chocolate and peppermint. This time of year I typically turn to peppermint bark to get my fix, but this year wanted to try something new and fun. I’ve experimented with some different types of whoopie pies recently (pumpkin, red velvet, and s’mores) and thought that a peppermint whoopie pie would be fun and festive. They turned out just as awesome as I thought they would. The chocolate cakes are soft and moist, and are filled with a peppermint-spiked buttercream frosting. For a Christmas-y kick I rolled the the edges in crushed candy canes. I kind of think Santa would go bananas if he found these on a plate with a glass of milk on Christmas Eve!

The tops of my cakes got a little crackly because I used a cookie scoop (medium size) to scoop out the dough, but if you wanted a smooth top you could wet your finger a little and dab the top for a smoother finish. I don’t mind my cookies having character :)

If you have kids, do you leave the same kinds of favorite cookies every year or do you change it up?

Four years ago: Buckeyes

Peppermint Whoopie Pies

Yield: 24 whoopie pies

Prep Time: 15 minutes

Cook Time: 10 minutes

Total Time: 45 minutes

A festive holiday twist on traditional whoopie pies.

Ingredients:

For the Cakes:
1-2/3 cups all-purpose flour
2/3 cup unsweetened cocoa powder
1½ teaspoons baking soda
½ teaspoon salt
4 tablespoons unsalted butter, at room temperature
4 tablespoons vegetable shortening
1 cup dark brown sugar
1 egg
1 teaspoon vanilla extract
1 cup milk

For the Filling (Peppermint Buttercream):
2 cups powdered sugar
4 tablespoons unsalted butter, at room temperature
3 tablespoons heavy cream
2 teaspoons vanilla extract
½ teaspoon peppermint extract
½ teaspoon salt
Crushed candy canes, to garnish

Directions:

1. Make the Cake: Preheat oven to 375 degrees F. Line two baking sheets with parchment paper.

2. Whisk together the flour, cocoa powder, baking soda, and salt in a medium bowl. In the bowl of a stand mixer fitted with the paddle attachment, beat together the butter, shortening and brown sugar on low speed until just combined. Increase the speed to medium and beat until fluffy and smooth, about 3 minutes. Add the egg and vanilla and beat for another 2 minutes.

3. Add half of the flour mixture and half of the milk to the batter and beat on low until just incorporated. Scrape down the sides of the bowl. Add the remaining flour mixture and ½ cup milk and beat until completely combined.

4. Drop about 1 tablespoon of batter onto one of the prepared baking sheets and repeat, spacing them at least 3 inches apart. Bake one sheet at a time for about 10 minutes each, or until the pies spring back when pressed gently. Remove from the oven and let the cakes cool on the sheet for about 5 minutes before transferring them to a rack to cool completely.

5. Make the Filling: In the bowl of a stand mixer fitted with the paddle attachment, beat together the powdered sugar and the butter, starting on low and increasing to medium speed, until the mixture is crumbly, about 1 minute. Add the heavy cream, vanilla, peppermint extract, and salt and beat on high until smooth, about 3 minutes.

6. Assemble the Whoopie Pies: Spread filling onto the flat side of one cake using a knife or spoon. (Alternatively, you can use a pastry bag with a round tip to pipe the filling onto the cakes, which will give you a smoother, neater presentation.) Top it with another cake, flat-side down. Repeat wit the rest of the cakes and filling. Roll the edges in crushed candy canes.

7. Whoopie pies are best eaten within a day of making them. Store in a wide, shallow container arranged in a single layer for up to 3 days. You can also wrap them individually in plastic wrap.

(Recipe adapted from Whoopie Pies)

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73 Responses to “Peppermint Whoopie Pies”

  1. Pat Marquez on December 15, 2011 at 12:19 am

    Love Whoopie Pies…cant wait to try this recipe. Thanks….

    Reply

  2. CouponClippingCook on December 15, 2011 at 1:11 am

    I love the crakly cake look! They are so pretty! I’m certain that Santa would go bananas if he saw these. They look sooo delicious!!! Beautiful pictures.

    Reply

  3. Brandie (@ Home Cooking Memories) on December 15, 2011 at 1:46 am

    I love just about any dessert with peppermint…the candy canes look so great on the edges.

    Reply

  4. Autumn on December 15, 2011 at 5:29 am

    Well, I refuse to make whoopie pies but I can’t wait to make these GOBS! Giving a big batch to my dad for Christmas! =)

    Reply

  5. Kiri W. on December 15, 2011 at 6:01 am

    Looks fabulous! Still haven’t had my inaugural whoopie pie, I just can’t seem to find them anywhere but Starbucks, and that seems like it won’t be impressive…

    Reply

  6. linda on December 15, 2011 at 6:30 am

    your whoopie pies are beautiful! i love the crackly tops & i agree with you much more character!
    prepared your dough for pecan tassies & put in freezer so i can stay ahead for xmas day!

    Reply

  7. Katrina on December 15, 2011 at 7:24 am

    These are so pretty!

    Reply

  8. Jennifer@Peanut Butter and Peppers on December 15, 2011 at 7:37 am

    Ok, I so don’t like you! Why, why, why must you do this to me? I try so hard to be good, and then you post these delightful cookies! Ok, fine I’m making them this weekend. Do you think they would ship well? I never shipped frosted cookies. Ok, I just looked one more time at your cookies, yes I must make them!!

    Reply

  9. Kate K on December 15, 2011 at 7:59 am

    You read my mind. I was so close to buying a mix for these yesterday and voila–a recipe instead :) Thank you kindly.

    Reply

  10. sue@ cakeballs, cookies and more on December 15, 2011 at 8:32 am

    I have fallen in love with whoopie pies, they are so tasty!

    Reply

  11. Jill Lombardo on December 15, 2011 at 8:38 am

    Oh My! Those look fantastic!

    Reply

  12. Tara on December 15, 2011 at 8:39 am

    I made these last Christmas and they were super yummy! I love the crackle… makes the cookie look more appetizing!

    Reply

  13. Rachel @ My Naturally Frugal Family on December 15, 2011 at 8:50 am

    I have yet to make whoopie pies but everytime I see them I think that I should.

    Yours are just gorgeous!

    Reply

  14. LaurBucks on December 15, 2011 at 8:59 am

    Who doesn’t like a little Whoppie Pie in their life? lol. These look scrumpshish!

    Reply

  15. Amy @ The Savvy Kitchen on December 15, 2011 at 9:21 am

    Those pies look great!

    Reply

  16. Martha in KS on December 15, 2011 at 9:29 am

    Where are the winners posted for the last 3 giveaways? I don’t want to miss my name being announced.

    Reply

    • Michelle on December 16th, 2011 at 12:23 am

      Hi Martha, The original posts are updated with the winners at the top (with the exception of the Fiesta giveaway, there is a bug in that code for some reason and I’m working on getting it fixed, when I update it the post crashes). However, the winner is always also emailed.

      Reply

  17. Mercedes (Satisfy My Sweet Tooth) on December 15, 2011 at 9:39 am

    These whoopies are amazingly adorable and scrumptious!

    Reply

  18. Bev Butler on December 15, 2011 at 10:03 am

    Cookies look delish!

    Reply

  19. Amberly on December 15, 2011 at 10:23 am

    These look delicious! Maybe I’ll have to make them for Christmas this year!

    Reply

  20. Ashli on December 15, 2011 at 10:37 am

    Those look amazing and I love the crackles! I don’t know who wouldn’t:) We pretty much leave the same cookies each year for the Big Man…sugar cookies…but I may make these this year for Christmas Eve and ask the little one if we could leave just one of them for Santa this year for something new:) Merry Christmas BEB!! :)

    Reply

  21. Ashley @ Wishes & Dishes on December 15, 2011 at 10:45 am

    These look so festive and perfect!!!

    Reply

  22. Shirley on December 15, 2011 at 10:54 am

    Whoopie Pies are one of my most favorite cookie.

    Reply

  23. Ally on December 15, 2011 at 10:59 am

    You’ve done a fantastic job… these look great!!
    xo

    Reply

  24. Erin @ Dinners, Dishes and Desserts on December 15, 2011 at 11:45 am

    These look amazing! I love all things chocolate and peppermint this time of year! I like the crackly top!

    Reply

  25. MaryBeth Weissman on December 15, 2011 at 12:08 pm

    I am going to try these over the weekend…can’t wait!

    Reply

  26. Mary @ Bake Break on December 15, 2011 at 12:29 pm

    These look amazing! I’m wishing peppermint season wasn’t so quickly coming to an end!

    Reply

  27. Jessica on December 15, 2011 at 1:18 pm

    These look incredible! My kids love whoopie pies so I am sure they will love these. We have a few favorite cookies we make every year, along with our favorite fudge but we are always looking for something new to try. We made red velvet whoopie pies last year and they were a huge hit. I can’t wait to try these. Thanks for the great post :)

    Reply

  28. Jeanne on December 15, 2011 at 1:29 pm

    Wow! I know that this will be my favorite whoopie pie flavor combination ever! I must try this.

    Reply

  29. Sarah on December 15, 2011 at 2:41 pm

    This looks delicious and cute! I would love if you shared this in my holiday dessert recipes Blog Hop. Enter it for a chance at a Wilton Pre-Baked Gingerbread Cookies Decorating Kit! http://www.recipelionblog.com/december-blog-hop-holiday-dessert-recipes-giveaway

    Sarah @ RecipeLion

    Reply

  30. Megan on December 15, 2011 at 3:07 pm

    Yum! I can’t wait to make theses.

    Reply

  31. Estella on December 15, 2011 at 3:18 pm

    I’ve tried these before but using the shortcut method and doing the cake mix instead. lol
    They are sooo cute when you do them mini sized and you can do them in so many colors for special occasions/holidays. Love the peppermint look!
    TFS

    Reply

  32. Liren on December 15, 2011 at 3:27 pm

    Love these :) I bet Santa would never leave if there was a plate left for him!

    Reply

    • Casey on December 15th, 2011 at 3:47 pm

      whoops, commented on the wrong thing! lol but these look and sound delis :)

      Reply

  33. Gail @ Faithfulness Farm on December 15, 2011 at 5:00 pm

    Crackled tops is simply PERFECT — just what they should look like. I’m going to try these soon :)

    CHRISTmas Blessings!
    Gail

    Reply

  34. Janet@FCTC on December 15, 2011 at 5:07 pm

    Ooo, these look good. I tend to go nuts over minty foods at Christmas and these look soooo good!

    Reply

  35. Valerie on December 15, 2011 at 5:13 pm

    Chocolate and peppermint, one of my favorite combinations. I love making whoopie pies but never even considered this combo. Thanks for sharing.

    Reply

  36. Anna on December 15, 2011 at 6:49 pm

    These look great! What do you do with all the stuff that you make? Every time I see something new on your blog this question comes to mind. I don’t believe you and your family can eat all of this.

    Reply

    • Michelle on December 16th, 2011 at 12:21 am

      Hi Anna, A little bit of everything. Sometimes I only make a 1/2 batch of something, sometimes I freeze leftovers. I share with my mom, sister, my boyfriend. My mom often will take things to work to share with her coworkers. If I have a lot of something and the timing is right, I’ll give them to my grandma to take to the food bank or Meals on Wheels, where she volunteers.

      Reply

  37. Teresa Norris on December 15, 2011 at 7:11 pm

    These look amazing…. I love chocolate and peppermint!

    Reply

  38. Bri on December 15, 2011 at 7:32 pm

    These look amazing, I adore the flavor combination of chocolate and peppermint and have no idea why I only eat it during Christmas time!

    Reply

  39. Tiff on December 15, 2011 at 8:39 pm

    Clever take on the whoopsie pie!

    Reply

  40. Eric Noak on December 15, 2011 at 9:33 pm

    Wonderful as usual!

    Reply

  41. Juliet on December 15, 2011 at 10:23 pm

    Yum!!

    Reply

  42. Ann on December 15, 2011 at 11:16 pm

    Yum! May curb my Jonesing for peppermint ice cream!

    Reply

  43. Ann on December 15, 2011 at 11:54 pm

    You’re absolutely right – peppermint whoopie pies were a great idea! Thanks – they look amazing! ….Also, thanks for doing this 12 days of Christmas giveaway -it’s been terrific fun!

    Reply

  44. Mackenzie@The Caramel Cookie on December 16, 2011 at 8:14 am

    Mmm these are perfect for the holidays!

    Reply

  45. angela on December 16, 2011 at 9:19 am

    My hubby would be so happy with these. He loves peppermint. I would like to give whoopie pies a whirl and I’m thinking gingerbread. Maybe I can tweak your recipes.

    Reply

  46. Jamie (Thrifty Veggie Mama) on December 16, 2011 at 11:55 am

    These looks so delicious!

    Reply

  47. Karen Platt on December 16, 2011 at 1:16 pm

    Hi – I just found your site and look forward to learning oh, so much from you! I just subscribed to your facebook site and your email site as well. My mom made a version of Whoopie Pies when we were growing up, only we called them Gobs….

    Reply

  48. Christine on December 16, 2011 at 2:11 pm

    Look sooo good!!

    About how many candy canes did you have crushed up for these?

    Reply

    • Michelle on December 16th, 2011 at 6:38 pm

      Hi Christine, I honestly don’t remember, I think maybe 5 or 6.

      Reply

  49. Niki Scott on December 16, 2011 at 7:30 pm

    Do you think you could scoop the dough into rounds and then freeze them that way? Pull out a dozen or so and make them instead of the entire batch? Just wonderin’….cannot wait to try these! Love your site!

    Reply

    • Michelle on December 26th, 2011 at 5:31 pm

      Hi Niki, I think you might be able to do that, since it works well for cookies. I haven’t tried it though, so can’t vouch for it.

      Reply

  50. Katie@Will Race for Carbs on December 16, 2011 at 10:18 pm

    I made these tonight and they were fantastic!! The frosting was so good I could have eaten the whole bowl….but I restrained myself! I saw them the other day on your facebook post and thought, “I need to make these!” I even put on my blog that I was going to make them. Thank you, thank you for this great recipe. I am sure I will make it for years to come!

    Reply

  51. Aimee on December 17, 2011 at 4:50 am

    Hi Michelle, your whoopie pies ALWAYS look so cute and delicious. I’ve made your pumpkin whoopie pies before for a potluck and they were a huge hit! I think your peppermint whoopie pies would make an excellent holiday gift! Is vegetable shortening absolutely necessary? or can I substitute it with butter? If so, how much butter would you recommend? Thank you so much for sharing your recipe!

    Reply

    • Michelle on December 17th, 2011 at 8:16 pm

      Hi Aimee, Thank you! I tend not to substitute butter for shortening in recipes just because they do have very different properties when used in baking. The vegetable shortening helps cookies and baked goods retain shape.

      Reply

      • Aimee on December 18th, 2011 at 2:12 am

        Oh i see, okay then. Thank you Michelle for responding so fast! Can’t wait to get started on these! Happy Holidays to you!

        Reply

  52. Casey on December 18, 2011 at 12:35 pm

    Love the filling. My grandchildren would love this.

    Reply

  53. Sonya on December 18, 2011 at 8:36 pm

    I made these over the weekend…amazing! I made one minor change, a layer of chocolate ganache between the whoopie pie and the filling :)

    Reply

  54. Diana on December 20, 2011 at 12:49 am

    This looks amazing but I have a concern, I don’t have a mixer like the one you mention, I don’t have a paddle attachment like the one you speak of either…would it be fine to use a traditional hand mixer like this one: http://www.amazon.com/Proctor-Silex-62515-5-Speed-Mixer/dp/B00006IUWY/ref=sr_1_23?s=kitchen&ie=UTF8&qid=1324360061&sr=1-23

    I hope I can still make these :)
    Thanks! ~ Diana

    Reply

    • eric on December 20th, 2011 at 9:27 am

      diana, i don’t have the tools mentioned either. i actually mixed the buttercream by hand using a whisk, and it was easy to do.

      Reply

      • Michelle on December 20th, 2011 at 6:44 pm

        Hi Diana, Ditto Eric – You can definitely use the equipment you have at your disposal.

        Reply

  55. Kelly on December 22, 2011 at 1:27 am

    I made these today since I was stuck at home. They came out really great! The ‘cookie’ part was nice and moist and the amount of peppermint extract in the icing wasn’t too overpowering. I was rather confused at the consistency of the icing mixture when it was just butter and sugar at first, but found that adding the cream made it more recognizable. After making a batch of these, my friends (which included one who can’t stand peppermint) came over real-quick and devoured them before my parents got home try them out for themselves. Thank you for sharing this! 8D

    Reply

  56. Kevin (Closet Cooking) on December 31, 2011 at 3:37 pm

    These whoopie pies look amazing!

    Reply

  57. marla on October 4, 2012 at 9:20 am

    When you have a quickie moment check out details for the Chocolate Adventure Contest I have posted at FFC ~ I am sure you could come up with AMAZING submissions! This is the kinda thing that would be perfect :)

    Reply

  58. Mallory on November 24, 2012 at 12:46 pm

    These were delicious!! I honestly don’t normally love whoopie pies, I’m not big on cake or buttercream but I wanted to make them because they just looked so festive. They had the perfect amount of peppermint flavour, they were moist and adorable. I think there should’ve been a little more buttercream, but other than that they were amazing.

    Reply

  59. Pam Lambert on December 9, 2012 at 12:24 am

    Would you be able to freeze the cakes w/o the frosting and use them when you wanted to?

    Reply

    • Michelle on December 9th, 2012 at 10:53 am

      Hi Pam, Absolutely! Enjoy!

      Reply

  60. Tiffany on December 11, 2012 at 7:44 pm

    Wow! These are beautiful! I bought large stocking stuffers in the shape of a candy cane tube that is filled with pb cups. Now I know just what to do! “oh what fun”!

    Reply

  61. Leah on December 16, 2012 at 11:36 am

    I made these last night and they were delicious! And not nearly as hard as I thought they would be. I’m starting to get tired of the cupcake so I can’t wait to try whoopie pies again. Next mission – red velvet. My only complaint is that the filling wasn’t nearly enough for all the pies I made. But still, they were sooo good :)

    Reply

  62. Alison on December 14, 2013 at 4:16 pm

    These were delicious and my favorite part was the recipe makes the PERFECT amount of filling. I literally scraped the bowl to fill the last whoopie pie! I am so sick of recipes that leave me with a bowl full of unused frosting! :)

    Reply

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