Mint chocolate Milano cookies are crisp and buttery homemade treats. These cookie sandwiches are filled with peppermint and orange-infused dark chocolate. A perfect holiday dessert or for a cookie exchange!
I always looked forward to going to the market with my mom because she let me pick one thing to bring home as a special treat. Nine times out of ten, it was Pepperidge Farm Milano cookies, or these anise cookies. Each bag contained elegant crunchy butter cookies filled with dark chocolate.
Each treat came with two cookies tucked into white paper liners because they knew you couldn’t just eat one. Cookies + Chocolate = Win-Win! This year I decided to make these at home. Keep reading to see how they turned out. Warning. You may be tempted to make your own too!
The Milano cookie base is a mixture of flour, butter, sugar, and eggs. It’s a thick pipeable batter that creates tender and crunchy cookies. I used a resealable plastic bag and cut a 3/4-inch hole to create the oval-shaped cookies. The surface won’t be entirely smooth but will even out as they bake.
I made this recipe two ways, with all-purpose flour and gluten-free flour. I found that the regular flour gave a thinner cookie that was slightly more crunchy, like the commercial kind. The gluten-free cookies were a little thicker and needed a minute or two longer to bake. Both were delicious. It’s nice to have options!
There is something about the smell of melted chocolate that makes me instantly happy. Don’t you agree? I used Ghirardelli 60% cacao bittersweet chips and added a hint of peppermint extract and fresh orange zest for a little more zing to the cookie. If you are making this recipe gluten-free, make sure to find chocolate that has been certified.
After filling a few cookies, I found that the warm chocolate caused the cookies to slide apart after sitting for a few minutes. Seeing this was becoming a hot mess, I tried a different filling method.
I applied the melted chocolate to one side of the cookie and let it cool at room temperature for about 10 minutes before adding the tops. This helped the tops stay put once cooled and then lightly pressed together.
Allowing the chocolate to cool once spread onto the cookie lets the chocolate set faster. For extra insurance, you can refrigerate the cookies with the tray on a flat surface for a few minutes after cooling and assembling.
So who will be lucky enough for you to share a cookie or two with? I put these cookies out on the dessert table after my holiday feast and guess what? My stepmom Lynne thought they were store-bought!
Haha, who knew these sneaky Milano impostors, could trick unsuspecting tasters. These are fun to make and are great as homemade gifts, cookie exchanges and dip in a hot cup of coffee or tea. I hope these make it to your cookie must-have list!
How do you make cookies of the same size?
The trickiest thing about this recipe is piping the cookies. For the first few cookies in each row, I marked with pencil on the parchment paper 2-inch long sections so I could try to make them consistent in length. You can then flip over the paper so you can see the outline but not get the markings on the cookie. After you pipe a few, you get into a rhythm. Try your best to get similar lengths and widths because they need to be matched up to connect together. But don’t worry if you have a few odd pairings. It makes it look more homemade, and no one will complain after they taste the first bite!
Mint Chocolate Milano Cookies
Ingredients
- 2 ½ cups all-purpose flour
- 1 teaspoon kosher salt
- 1 cup unsalted butter, softened, 2 sticks
- 1 ⅓ cups granulated sugar
- 2 large whole eggs
- 1 egg white
- 2 teaspoons vanilla extract
- 8 ounces chocolate chips, bittersweet
- 1/2 teaspoon peppermint extract
- zest of one orange, (optional)
Instructions
- Preheat oven to 325° F. Line two baking sheets with parchment paper.
- Combine flour and salt together in a medium-sized bowl and set aside.
- In the bowl of a stand mixer on medium speed, cream together butter and sugar about 30 seconds.
- Add in whole eggs, egg white, and vanilla. Continue to mix on high until light and fluffy, about 1 minute, scraping sides of the bowl as needed. Lower speed and gradually beat in flour mixture until just incorporated.
- Transfer batter to a pastry bag or resealable bag with a ¾-inch hole snipped in one corner. Pipe batter into 2-inch long strips, ¾-inch wide.
- Bake for 13–15 minutes, or until the edges of the cookies just begin to brown. Remove from the oven and let it cool on the baking sheet for 5 minutes, then transfer to a cooling rack. Allow cookies to cool completely. Arrange cookie halves in pairs of similar shape and size.
- Melt chocolate in a double boiler until smooth, stir in peppermint extract. Remove from heat and let cool for 10 minutes.
- Spoon ½ to 1 teaspoon chocolate onto one cookie half and sprinkle with a pinch of orange zest. Repeat with half of the other cookies.
- Place cookies on a baking sheet and allow to cool for 10 minutes. Gently press the other half on top until the chocolate just reaches the edges.
- Let the sandwiches sit until the chocolate has set, you can refrigerate them to set the cookies quicker if needed.
Recipe Video
Notes
- Store extra cookies in an airtight container for up to 2 days, or in the freezer and defrosted for an hour before serving.
Nutrition Facts
Percent Daily Values are based on a 2000-calorie diet. All nutritional information is based on estimated third-party calculations. Each recipe and nutritional value will vary depending on the brands you use, measuring methods, and portion sizes per household.
CakePants says
I wouldn’t have thought to pair peppermint extract and orange zest, but these look fantastic! That’s such a sweet little tradition you and your mom had at the store.
Jessica Gavin says
Thank you CakePants! The orange is pretty subtle and the mint anhances the flavor of chocolate just the right amount. I think it was the only way for my mom to keep me calm while she shopped, hehe.
brita says
Jessica these look SO good! I adored these growing up (and still do). Definitely saving this to cook over my Christmas break. Beautiful pictures as well!
Jessica Gavin says
Thank you Brita! There are definitely some cookies that are nostalgic that I will always love! Let me know if you get a chance to make the recipe 🙂
Tiffany says
I’ll definitely be trying these soon! I grew up on those cookies and can’t get enough of them. Yours look delicious!
Jessica Gavin says
Thank you Tiffany! I would love to hear how yours turn out 🙂
Angie says
I think you forgot to mention when to add the peppermint extract, but I assume it’s added to the melted chocolate.
Thanks, they look delicious.
Jessica Gavin says
Hi Angie- Thank you so much for the comment! I updated the recipe with the changes 🙂
Rica says
These look delicious! I have a few questions though. Some recipes mix heavy cream with the chocolate. How do you think this affects it? Also, some recipes make use of powdered sugar instead of granulated sugar. Does this make a difference? And lastly (hehe), does using white eggs instead of the whole egg make a difference? I saw other recipes using just white eggs. Hehe i can’t wait to hear back!
Jessica Gavin says
Love all of the food science questions Rica! Mixing cream and chocolate creates a luscious chocolate ganache. The chocolate will be a little softer once cooled so it won’t have the chocolate “bite”. It’s totally up to you which texture you prefer. Granulated sugar is better for creaming with butter if you are trying to add some air into the cookie batter. Granulated sugar will also make you cookies more crisp, powdered sugar tends to make cookies a little more chewy but may hold shape a little better. Egg whites are mostly protein so it will give a crisp and drier cookie. If you include the egg yolk it will give a more tender cookie, richer flavor and more golden color. I hope that helps!
Mika says
They are good but I will use 1cup of sugar instead. I didn’t use orange zest. Definitely keeping this recipe. Thanks for the recipe!?❤
Sophie says
Hi, I’m trying to use this quarantine time to experiment with baking and want to make these to send my family. Are the pictures the regular or GF version? I like your recipe most, but the cookies look thick. And is the 3/4″ hole in the ziploc just literally the length of the cut I make? Or do I have to calculate diameter? And do you have any tips for shipping/making them last so my family can enjoy them a few states away? Thanks a lot, I can’t wait to try these!
Jessica Gavin says
Hi Sophie, great questions! The picture is the gluten-free version which was a bit thicker than the all-purpose flour (check out the video for that thickness). Yes, make the length of the cut 3/4-inch (when the bag is flat). Fo shipping, I would place a few in cupcake liners (if you have any) and then wrap each of those in plastic wrap, then place them in a resealable plastic bag, or plastic container would work even better. Make sure to put newspaper or the styrofoam popcorn to surround all sides of the box. Also, since these have chocolate you may want to put one of those durable ice packs in the box below the cookies or ask the shipping center the best way to keep them cool. Sometimes they can designate where to keep them in the trucks, room temperature and below is good.
Sophie says
Hi Jessica,
Thank you so much for the information! I will do all that 🙂
Dawn Caro says
I really want to try these. Certainly one of my favorites. I have found some wonderful flavoring emulsions that I love and feel they give a more honest flavor to the products I am making. I plan to use tat for the mint in here. And may try some raspberry as well. Thank you for all your information. I love knowing I can rely on your knowledge when I don’t have a clue sometimes! You are the Best!
Jessica Gavin says
Thank you, Dawn! I can’t wait to hear how to the cookies turn out with the flavor emulsions. I’d love to hear the result!