Start with 24 cupcakes that have been baked and completely cooled. You can use a chocolate box mix, or your favorite from scratch recipe. (I used my chocolate cupcakes recipe.) Place the cupcakes on a cookie sheet lined with wax paper. Make room for a second cookie sheet lined with wax paper in your freezer.
To prep the cupcakes: use a pairing knife to cut a large circle (about the size of a half dollar) in the top of the cupcake. Cut down almost to the bottom of the cupcake, then lift out the cut part. You should end up with a cone shaped chunk of cake. Slice the cone off of each of the cupcake pieces. (You need to make the piece of cake smaller, because the cupcake will be filled with ice cream.) See this post for photo instructions.
I suggest you prepare all the cupcakes for the ice cream, then place your second cookie sheet in the freezer. Work in batches of 3-4 cupcakes, filling with ice cream, then placing on the cookie sheet that’s in the freezer. That way the ice cream won’t melt out of the cupcakes.
Scoop about 1-2 tablespoons of ice cream into the center of each cupcake. Place the top back on and press gently. Put the cupcake on the cookie sheet in the freezer. Continue until all the cupcakes are filled and in the freezer.
Cover the cupcakes with plastic wrap (leaving them on the cookie sheet) and freeze for at least 4 hours before serving. You can place them (frozen) in a single layer in large Ziploc bags and freeze for up to 1 month before serving.
To make the frosting: beat butter with a hand or a stand mixer until smooth. Mix in powdered sugar slowly, then add vanilla and peppermint extract. Start with 1/4 teaspoon peppermint extract then taste and add more as desired. I used 1/2 teaspoon. Mix in 1 tablespoon of heavy whipping cream at a time, mixing well, until you’ve reached your desired consistency. I used 5 tablespoons of heavy whipping cream. Stir in food coloring and then chocolate chips.
When ready to serve, have your frosting ready. Remove a cupcake from the freezer, frost as desired, and serve immediately. Top with additional mini chocolate chips for garnish.