Move Over Cookies: Chocolate Peppermint Whoopie Pies Are Here for the Holidays

Sweet, festive, and surprisingly simple.

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This recipe was written in partnership with got milk?

When it comes to bringing the cheer, there’s nothing quite like a whoopie pie. Fun to say and even more fun to eat, this dessert features two round mounds of chocolate cake that sandwich a light, creamy filling. Is it a pie, a cake, a cookie, or a sandwich? Whatever it is, it’s delicious and deserves a spot in your regular dessert rotation.

The origins of the whoopie pie are hotly debated. Maine, Massachusetts, New Hampshire, Pennsylvania, and even Virginia all lay claim to its invention. In Pennsylvania, the whoopie pie is said to have originated from the Amish and Pennsylvania Dutch culture; in Massachusetts, “Whoopee Pies” were sold as far back as the 1920s. Whatever its provenance, a good whoopie pie is up there with the best and most satisfying pastries.

For the cake, we wanted to ensure a moist, tender texture. Instead of using water or lots of eggs and butter, we turned to a secret weapon: real milk. Of course, milk hydrates the starches in the cake batter just like water. But it also has a tenderizing effect on the texture of the cake. As an added benefit, real milk also provides nutrients like protein and calcium, as well as plenty of potassium, phosphorus, riboflavin, niacin, and vitamins D, B12, and A.

In the 1930s, one of the first cookbooks to feature an "Amish Whoopie Pie" included Marshmallow Fluff in the filling. Naturally, we followed suit. Beating butter and sugar forms the rich backbone of the filling, into which we carefully fold a measured amount of Fluff. A splash of peppermint extract brings these whoopie pies into holiday territory, but you can flavor the filling any way you wish.

All that’s left is to spoon some filling on a cake, top it off with another cake, smoosh it down, and eat it. Despite some careful technique, whoopie pies are surprisingly unfussy food. Making them is a rewarding project for your whole family and a fantastic way to ring in the holiday season.

Chocolate Peppermint Whoopie Pies

Yield: 6 pies
Active Time: 45 minutes
Total Time: 1 hour

For the Cake:
2 1/4 cups (10 1/8 ounces; 287g) all-purpose flour
1 cup (7 ounces; 200g) sugar
1/2 cup (1 1/2 ounces; 43g) cocoa powder
1 teaspoon (5g) baking powder
1/2 teaspoon (3g) baking soda
1/2 teaspoon (3g) salt
3/4 cup (180ml) whole milk
1/3 cup (80ml) canola oil
1 large egg
3 tablespoons (42g) unsalted butter, melted
1 teaspoon (5ml) pure vanilla extract

For the Filling:
8 tablespoons unsalted butter (1 stick), softened but still cool
1/2 cup (2 ounces) confectioners' sugar
1/2 teaspoon (3g) peppermint extract
1/8 teaspoon fine table salt
2 cups (192g) Marshmallow Fluff

Directions:

1. For the Cake: Adjust oven racks to upper-middle and lower-middle positions and heat oven to 350°F. Line 2 baking sheets with parchment paper.

2. In large bowl, whisk flour, sugar, cocoa, baking powder, baking soda, and salt; set aside. In medium bowl whisk together milk, oil, egg, butter, and vanilla. Pour wet ingredients into dry and whisk until smooth.

3. Grease a 2-ounce ice cream scoop or 1/4-cup measuring cup with vegetable oil spray. Scoop out 12 mounds of batter onto prepared sheets, spraying scoop or cup between mounds. Bake until firm to touch, 12 to 14 minutes, rotating pans from top to bottom and front to back halfway through baking. Transfer parchment sheets (with cakes still attached) to wire rack to cool completely.

4. For the Filling: In the bowl of a stand mixer fitted with a paddle attachment, beat butter and sugar at medium speed until fluffy, about 2 minutes. Beat in peppermint extract and salt. Beat in Fluff until incorporated, about 1 minute longer. Refrigerate filling until slightly firm but spreadable, about 15 minutes.

5. Spoon or pipe filling between half of the cakes. Sandwich together with remaining cakes.

6. Enjoy with a large glass of real milk!