Chocolate Peppermint Sandwich Cookies

CATEGORIES: Christmas, Cookies, Sara

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.



    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!

  1. 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!

  2. 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.

  3. 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???

  4. 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!!

  5. 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)?

  6. 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!

  7. 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!

  8. 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!

  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!

    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.

  10. 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 🙂

  11. 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!

  12. 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!

  13. 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!

  14. 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” 🙂

  15. I made these last night hoping they would make a good item for my open house and I loved them. Thank you!

    I had one problem with them. When I mixed them up the dough was very crumbly. In order to keep them together I compacted the dough into a measuring spoon pretty tightly – no other way would keep them together. When I cooked them they held the measuring spoon shape.

    I definitely use a large egg in the recipe, but found that if I used another 1/2 to whole egg they turned out wonderful and brownie-ish as you described. I don’t know if it was elevation or if your large eggs are larger than mine or what, but I thought saying something might help others with the same problem.

  16. We just made these… and they turned out amazing! Instead of regular chocolate chips, though, we used mint chocolate. Yeah, winner! Since the cookie turned out so wonderfully minty, we left the frosting plain and it was the perfect combo.

  17. Chocolate and mint are my favorite combo! My daughter, Abby and I are going to try to make these for family Christmas. Thanx for a great website. Keep the ideas coming. Merry Christmas!

  18. Just made these last night w/the kids and they are so cute, fun, and just delicious!! LOVE that small size- I used my smallest cookie scoop (holds 1 TB) and cut those balls in half. They’re going to school for teacher gifts today.

  19. I made these using a tiny cookie scoop (melon baller actually), I’m not sure what size (I fit 24 on a standard cookie sheet) and I got exactly 2 dozen sandwiches. I had about half the frosting left over. I was fairly generous with the frosting and I’m not sure why I had so few sandwiches. Mine were maybe slightly larger than silver dollar size but I got nowhere near the 4-5 dozen sandwiches mentioned in the recipe.

  20. I just made these and they are AMAZING. I used dark chocolate chips (that’s what I had in the pantry) and with the peppermint it is perfection. I made them smaller than suggested, they are “bite sized” about the size of a quarter. Love them! I’m a new follower, and am loving your site! Thank you!

  21. This recipe did not turn out. The cookies spread out and made lacey edges, not at all like the photo here. I followed the recipe exactly and I’ve been baking for 10 years (I’m 25) and never had something come out so completely opposite from the recipe.

  22. I had never heard of your blog until I received a copy of your cookbook as a gift. After reading through it, I was so happy there was a whole blog full of your recipes in addition to the great ones in the book! I made these cookies today and they turned out perfectly! And seriously, what a fantastic cookbook! You have amazing recipes that use NORMAL ingredients! It’s definitely one of our favorite cookbooks.

  23. Can you make the chocolate cookie dough ahead of time and refrigerate it until ready to bake?
    Would it change the cookie at all? Thanks for the recipe. Tried it with sugar cookie dough and it was delish!

  24. Ohhhhhhh man! Are these good! I just finished making these and I am salivating thinking about eating another. I am doing a test run for a cookie party I am attending in 2 days, and these are the ones!!

    They took me awhile (maybe 2 hours from start to finish), but admittedly, I am a super duper slow baker (and cook, for that matter). I used a regular sized cookie scoop and quartered the scoop of dough. Then I pressed the dough lightly together, not into an exact ball- and I came out with some decent looking final cookies. I think my next run, I’ll press them ever so slightly so they are less rounded on the bottom when they are cool. Perfect little mini sandwiches, and I got to just shy of 4 dozen.

    For the frosting, I got impatient and just kept throwing in milk as I whipped it up. Not a disaster, but I overdid it and the frosting was not as creamy as it should’ve been.

    Overall, this is a GREAT special occasion cookie recipe for me. Thank you!!!!

    BTW- LOVE your site and asked my mom for your cookbook for Xmas. Hopefully she’ll deliver!! ; )

  25. I made these for a cookie exchange get together and everyone loved them! They turned out just like your pictures and the frosting in the ziplock bag works wonders!! thank you so much for a wonderful holday cookie!!!

  26. I just made the cookies – I don’t know if they will make it to the sandwich stage. I was in a hurry yesterday and made the dough ahead of time. This morning I simply put the container in a bowl of warm water and made the cookies as it the dough softened. At first I thought I had made a mistake – but they turned out perfect!

  27. Thanks so much for the recipe! We’ve made them twice so far (doubled the recipe the 2nd time!) When my hunter son saw the plate of little black rolled balls he asked if I was making deer poop. It stuck and now the younger kids call these cookies “reindeer poop” We love them!

  28. These look so fun and yummy! I love how you list “real butter” in your recipe- because unsalted butter, I agree, is just not real butter. 🙂

    1. My cookies also were not as flat, but they were still cute and tasted great so I didn’t mind. The last cookies sheet of my 3rd patch I forgot about and it was in the oven several minutes too long, and those cookies were flat, but still soft and chewy. I tried so hard not to overbake them – but in the end they worked better for me when baked longer. Maybe that will help you.

  29. I just whipped up a batch of these for a dinner party tonight. Oh my, so delicious. I just might skip dinner and eat just the cookies!

  30. Just made these with my 3 kiddos (3, 5, and 6). They LOVED helping roll the cookies in broken candy canes. Soooo yummy and so much fun for me and the kids. Thank you! These will definitely be a Christmas-time tradition!

  31. When I bake my chocolate chip cookies I use Pillsbury flour because, for some reason, that is the only flour that makes them puff up nice and fluffy and they won’t fall after they’ve cooled. When making these cookies, you WANT them to be flat so you can stuff ’em… I learned the hard way that making them with my flour doesn’t work out so well. Just a hint 🙂 I had more of a chocolate peppermint sandwich cookie ball thing going on ha ha

  32. Hi I was planning on making this recipe for Valentine’s day as a cute gift to give away and I was planning on subsituting the frosting with ganache but I noticed that you never stated the yield of frosting you get. So if you do figure it out could you please let me know.

  33. I just did these wonderful cookies for this upcoming Valentine’s Day. They taste yummy and they look sooo pretty! I’ll do them again for next XmAs (trying my Xmas recipes throughout the year). I did a vanilla frosting and it was excellent. I’ll try with peppermint extract for Xmas. Thank you for this awesome recipes!!!

  34. I’m sitting here thinking hmm… other flavor combos for the rest of the year?? Then I think, duh, St. Paddy’s day is coming up, I’ll make them peppermint just tint them green like the yummy mint brownies.

  35. I really wanted to like these cookies. In fact, I’ve made them twice in hopes that they would turn out better the second time, but I thought they were kind of meh. I used high quality semi-sweet chocolate chips, but I thought the chocolate flavor was very muted and kind of bland. The frosting was delicious, though!

  36. These are fabulous! The instructions were very well written and helpful. I do enjoy icing cookies so I tried the bag idea but did better with my little dip knife to ice. They are very easy and so fun to make and are definately a great addition to my Christmas cookie list. Great pictures too!

  37. These look delicious! I’m going to try them for Christmas. How should I store them if I make them a day or 2 in advance? Just an airtight container, or in the fridge? Thanks!!

  38. Please tell me what you did to get your cookies so flat! I just did a test run for Christmas and they came out so thick, and didn’t flatten out. They taste great but for some reason didn’t get nice and flat like yours. What am I doing wrong??

    1. I made these over Christmas and had the same problem a few others mentioned with the cookies not coming out flat. They still tasted great but just didn’t look quite as cute! The only thing I can think of is the salted vs. unsalted butter. Sara mentioned using salted butter and reducing the extra salt called for in the recipe, but then I wasn’t sure if she made that modification in the final recipe or not. I used salted butter AND the additional 1/4 tsp. it called for– was that correct? I’ve always assumed that when a recipe calls for “butter” it means the salted kind, but maybe that’s wrong.

  39. I need to make the frosting green for a grinch Christmas party. Can I just do a cfrosging ream cheese frosting? Any frosting recipe substitute ideas? Thanks! Cant wait to try them!!

  40. I made these for a Christmas party but let my daughter’s boyfriend (16 and loves homemade cookies!) taste test them the night I made them. He approved and ate a bunch of them–and so did my husband and then everybody else! I made the small, silver dollar-sized cookies and left them in a minute or two longer than the recommended baking time. They were perfectly flat and chewy.

    The frosting was terrific. It was hard to wait until the cookies were completely cool to frost them, but definitely necessary. Thanks for the great recipe!

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  42. We love peppermint! And i specifically love peppermint cupcakes! This is a new variation and we would definitely try this when we get back home! Love it!

  43. These are seriously my favorite dessert ever. Like no exaggeration whatsoever. Then this devastating thing happened that I had to stop eating gluten because of some health problems and my world came crashing down because how could I live without these cookies?? But then I got brave and tried making them with a gluten free flour blend (the one I used was Pamela’s) and guess what?! They totally turned out! I shared with my neighbors and no one even guessed it and they all raved over them. So for any of your gluten free fans….they can still have these!!! And all is right in my world again.

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