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. 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 what 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 let 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 to 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 sandwich 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!
Homemade Mint Chocolate Milano Cookies
- 2 1/2 cups all-purpose flour, or gluten-free flour
- 1 teaspoon kosher salt
- 1 cup unsalted butter, softened, 2 sticks
- 1 1/3 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)
- 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 a large bowl on medium speed, cream together butter and sugar about 30 seconds.
- Add in whole eggs and egg white, and then vanilla, and continue to beat on high until light and fluffy, about 1 minute, scraping sides of bowl as needed.
- Lower speed and gradually beat in flour mixture until just incorporated.
- Transfer batter to a resealable bag with a 3/4-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 oven and let cool on the baking sheet for 5 minutes, and then transfer to cooling racks.
- 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 cookie 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 the cookies to set the cookies quicker if needed.