Chocolate Peppermint Sandwich Cookies

So, strangely enough one of the cookies I make the most at home isn’t postedhere on the blog.  I’m sure many of you are familiar with the beloved “Homemade Oreos” most often made with cake mix cookies (and ohhh my gosh I didn’t even remember we had that link up.  Talk about lost old post!  It was written in June of 2008, when our blog was a whopping 3 months old and it’s totally old school, I love it)  and a yummy cream cheese frosting, like this.  And my most favorite thing to do is make the Christmas version with peppermint extract.  I’ve been on the hunt for a long time for a non cake-mix version of the cookie.  There’s tons out there and I’ve tried many and haven’t found exactly what I was looking for.  They were often cakey or too crispy, or too whoopie-pie-ish.  I wanted soft, but chewy with a sweetness that wasn’t overwhelming when sandwiched with frosting.  I was excited when I spotted this recipe on Cooks’s Country this week and made it right then and there.  It’s exactly what I was looking for; I love it when that happens. The cookies are not only adorable (I made mini cookies) but they have the perfect almost brownie-like texture and flavor, with a slightly chewy outside and soft center.  Cook with me!

Interestingly enough, these start more like a brownie than a cookie.   You just melt some butter, brown sugar, chocolate chips, and a little water on the stove until it melts.  The recipe calls for unsalted butter, but I’m way too lazy to buy more than one kind of butter at the store so I just use regular salted butter and then cut back on the additional salt called for.

When it gets all melted and smooth (just takes a couple of minutes) beat in an egg, and then add flour, salt, and baking soda.

The dough is really soft.  Do not do not do not add more flour.  If it’s too soft to work with, just let it sit for a few minutes to set up more (as the butter and chocolate comes to temperature it firms a bit) or even pop it in the fridge for a few.  But you’ll probably find like I did that you just need to be gentle and you can drop the dough onto your cookie sheet just fine.

Dough Tip: It’s really important when making sandwich cookies to make the cookies a uniform size.  You can measure out the dough, or use a cookie scoop.  When I make sandwich cookies, I like to make them small.  I figure you’re already getting 2 cookies in there, so giant ones can be kind of overwhelming.  If I want small cookies, I use my cookie scoop and then just cut the dough so it’s even.  For these cookies I cut a scoop from a standard cookie scoop into four.  That’s pretty tiny! But the finished cookies were about the size of a silver dollar, which is where I wanted them.

Baking Tip: Now, the most important thing about these cookies is that you don’t over-bake them.  In fact, you want to under-bake them.  It can sometimes be hard with chocolate cookies because you can’t use color for a visual clue.  Instead look at the texture.  The cookies should be puffed up, and the edges just barely set but the centers still soft.  The cookies in the above picture have been sitting on the pan for a minute cooling so they’re starting to crack.  Once they cool completely, they flatten out and crackle like this:


Next step is the frosting.  Now, I’m not sure who exactly wrote this recipe, but we obviously differ when it comes to frosting because I quadrupled the frosting in the recipe to have enough for my liking.  Quadrupled! You can add food coloring if you like or leave it a cool wintery white.

Frosting Tip:  Here’s my tip for frosting; keep it on the thick side.  Like, just a little thicker than you think it should be.  With sandwich cookies, you don’t want it to smoosh out when you bite into them, so if you keep the cookies extra soft and the filling just a tiny bit firm, then it usually ends up being a pretty good match.  I also go a little strong on the peppermint extract because it mellows out once it’s combined with the cookies.

Assembly Tip:  Don’t spread frosting on each one.  Put your frosting in a ziplock bag and cut the corner off.  Place cookies that are close in size (because they’ll all be a little different) next to each other and pipe on the frosting, staying close to the edge.  It’s soooo much faster than spreading it on, especially if you’re doing a ton of little cookies like I did.  There should be enough to be generous, but don’t go too crazy or it will all just squish out.

Gently place the the top side of the cookie on, and then you can roll the edges in sprinkles if you want (it’s sometimes easiest to pour some sprinkles in the palm of your hand and roll the cookie through them.

You can find so many cute holiday sprinkles this time of year.  I have quite the sprinkle collection because I can’t pass them up!

Or try white frosting with cute blue sprinkles for a winter or Hanukkah look.

My favorite though, is crushed candy canes.  You only need one or two for a whole batch of cookies.

Pop them in some cute containers and you’re all set for giving (or munching!)

*Edit:  Several readers have asked, so for clarification- the recipe written below is altered from the original and includes all of my modifications, including the increased frosting amount.


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Meet The Author

Sara Wells

Sara Wells co-founded Our Best Bites in 2008. She is the author of three Bestselling Cook Books, Best Bites: 150 Family Favorite RecipesSavoring the Seasons with Our Best Bites, and 400 Calories or Less from Our Best Bites. Sara’s work has been featured in many local and national news outlets and publications such as Parenting MagazineBetter Homes & GardensFine CookingThe Rachel Ray Show and the New York Times.

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Questions & Reviews

  1. YUM! So excited to make these before Christmas! By the way, under the picture of your cookie dough it says “doug tips” instead of “dough tips” 🙂

    1. Well hey- if your husband or boyfriend is named Doug, then I have some tips for you too… 😉

  2. Perfect. I was looking for a chocolate/peppermint pinwheel recipe but couldn’t find one I was confident would turn out the way I wanted. These are even cuter and everything I have ever made from your site turns out perfectly!

  3. I made the original recipe from Cook’s Country and it was very tasty, but I think you are totally right about the amount of frosting…there was barely enough. I tinted mine green and used mint extract but by the time the cookies were filled, I wish I had at least doubled the filling part of the recipe. I did freeze some of them and they froze beautifully. I would like to try them again, smaller this time like you suggest. The originals were just a bit large. I just LOVE Cook’s Country!

  4. I followed the frosting amounts and had plenty, so my guess is it does not need to be quadrupled… although I had the same question!

  5. You are KILLING ME! I love mint and chocolate and these are now on the top of my list (out of like 20 things) to make next 🙂

  6. How are these in storage? Can I make them ahead and freeze? Frost and give away another day? Will they dry out?

    1. I haven’t tried freezing them, but if you wrap them well (or put in an airtight container) you could totally keep them in the fridge for a few days.

  7. I like to make sandwich cookies with gingersnaps and butter cream frosting. It’s a pretty tasty combination too.

  8. Have you ever tried using peppermint ice cream and then freezing them for a yummy cookie ice cream sandwich?

  9. oh perfect! I am so making this for a cookie exchange I am going to next week! I had been having a tough time figuring out what i was going to make and then I saw this..thank you!

  10. How perfect was this post! We totally love “homemade oreos” and I was thinking of doing this exact thing for my husbands work…I hadn’t thought of using peppermint extract though, I will have to try that. Thanks!

  11. thanks so much for sharing all of your recipes 🙂 this website is a great resource. love the creativity.

  12. I was just looking for the perfect something for my son to hand out to his preschool class and I just found it!! Question: You had mentioned you had to quadruple the frosting amount. I tend to always need extra frosting so the amount you’ve provided, is that the single or quadrupled amount? Thanks and I can’t wait to make these!

    1. I’m assuming not since there’s only 2 c powdered sugar and 1/2 c butter, but thought I’d ask.

      1. nope- that Is quadrupled! My recipe includes all of the adjustments I made to the original.

  13. Thank you, once again, for introducing my computer keyboard to drool! These look so yummy AND I’m SO SO SO happy the cream in the middle doesn’t have cream cheese in it (I was worried for a second). Best part – I have all the ingredients already! YAY!

  14. Lifesaver! Hurray, you read my mind. This is exactly what I was looking for. Like you, I have a ton of different sprinkles waiting to be used. Bingo!
    When you say you used a cookie scoop and then cut that in fourths, did you use the small one (about the size of a walnut? Mine says 50 on it)?

  15. I’m assuming the given frosting recipe is NOT quadrupled? Because we’d need to probably quadruple it too.

    1. No, that IS quadrupled. The recipe as written in my post includes all of my adjustments.

  16. My site is the same way…it seems like the recipes I make the most never make it to the blog!! I think I must like creating extra work for myself 😉

    These sound great, we love chocolate/peppermint combos!!

  17. I’m looking for a fun cookie to make with my 3&5 y olds. I don’t do cut outs or any kind of rolling out dough so that leaves out the obvious. Would the decorating part of this be too hard for little kids if I put the candy canes/sprinkles in ramekins? I’m thinking if I tell them to drive the wheel in the sprinkles, they should be able to make it work…

    Also, is this recipe already quadrupled or do I still need to quad the frosting as you’ve stated???

    1. Yeah, as long as you frost them all, and put plenty in and close to the edges so they can roll them. And yes, the frosting is already quadrupled from the original.

  18. You, Sara, are a problem. You have caused the most ridiculous peppermint/chocolate obeseeion in me. Just in the last week and a half i’ve made peppermint brownies (though I believe we can blame your Mom for that one?), peppermint kiss cookies, peppermint bark popcorn and I’ll be making these cookies tomorrow night. Also, I am so addicted I have made myself peppermint hot chocolate every single morning for the last two weeks because I just can’t get enough. I’m blaming you for the holiday weight gain! 🙂 I’m really not complaining though.

      1. Woo hoo! I drink peppermint hot chocolate just about every morning, haha. Glad to have another addict around here!

  19. Yay! I have always made these with the cake mix and one time I came across a whoopie pie recipe and thought, “oh cool, homemade oreos from scratch!” WRONG! Yeah, we weren’t big fans of the whoopie pie. I’m excited to try these out!!!

    1. Oh man, I felt like I would be publicly shunned as a food blogger if I admitted I wasn’t a huge fan of the whoopie pie- but I’m not either! lol Try these, they’ll make it all better!

  20. Thanks so much for this recipe. Just a few weeks ago I tried Candy Cane Oreos and loved them. Now I can make them at home whenever I need a fix.

  21. Yum, they look great! I wonder if the Cadbury egg chocolate sandwich cookies would turn out similarly? Or are they too chewy in your opinion?

    1. It’s really a different type of cookie. I do use those other ones (the cadbury choolate base) all the time for ice cream sandwiches. As long as you underbake them they work really great. But for frosting filling, this little cookie is a bit softer so it probably works a little better. Both taste amazing though!