This Chocolate Peppermint Cookie Cups creation has been a holiday staple in my kitchen for years. I first imagined these during a December afternoon when the house smelled of pine and my kids demanded something both chocolatey and minty. The contrast of a slightly crisp, deeply chocolate shell with a cooling, fluffy peppermint cream filling immediately won everyone over — they became the first treat to disappear at every party. I love that each bite delivers bright peppermint, rich cocoa, and a tender cookie texture that holds its shape but gives way to a soft center.

I discovered the balance of black cocoa for an almost-black appearance and Dutch-processed cocoa for rounded chocolate flavor after several tests. Using a scoop to portion the dough and pressing the centers while still warm creates a perfect cup to cradle the peppermint cheesecake filling. These are special because they travel well, make a beautiful platter, and give me a moment to add little festive touches like crushed candy cane or a dab of red color gel for that holiday pop.

Ingredients

• All-purpose flour: Use 2 cups of King Arthur or other trusted brands for consistent texture; measure by spooning into the cup and leveling for accuracy. It provides structure so the cups hold their shape when pressed.
• Dutch-processed cocoa powder: 1/4 cup adds depth and a smooth chocolate note; brands like Valrhona or Ghirardelli work well and reduce acidity compared with natural cocoa.
• Black cocoa powder: 1/4 cup gives an almost-black, dramatic color and an intense cocoa flavor; use for visual contrast and richer taste.
• Baking soda and salt: 1 teaspoon baking soda and 1/2 teaspoon salt balance rise and flavor; use accurate measuring spoons to keep chemistry precise.
• Unsalted butter: 1 cup at room temperature, preferably European-style unsalted butter for creaminess and higher butterfat — it makes the cookie tender and flavorful.
• Sugars: 1/2 cup granulated and 1 cup packed light brown sugar give caramel notes and moisture. Brown sugar keeps the cookie slightly chewy while granulated adds lift.
• Eggs and vanilla: Two large eggs and 1 teaspoon vanilla extract add structure, richness, and aroma. Use room-temperature eggs to help them incorporate smoothly.
• Heavy whipping cream: 1 cup cold for the peppermint filling; chilling the bowl and whisk makes it whip faster and hold peaks.
• Cream cheese: 8 ounces full-fat, room temperature for a silky, stable filling. Philadelphia or local artisan cream cheese both work.
• Peppermint extract and candy canes: 1 teaspoon extract for clear mint flavor and chopped candy canes for texture. Use clear extract to avoid cloudiness and adjust to taste.
• Red color gel: A small amount for festive dots on top — gel works best because it won’t thin the filling.

Instructions

Preheat and prepare pans: Preheat the oven to 350°F. Thoroughly spray two standard 12-cup muffin tins with nonstick cooking spray or brush with melted butter so the baked cups release easily. Having two tins ready lets you bake up to 24 cups at once. Combine dry ingredients: Whisk together 2 cups all-purpose flour, 1/4 cup Dutch-processed cocoa, 1/4 cup black cocoa, 1 teaspoon baking soda, and 1/2 teaspoon salt in a medium bowl. Sifting is optional but helps eliminate lumps and evenly distributes the cocoa. Cream butter and sugars: In a stand mixer fitted with the paddle or using a hand mixer, beat 1 cup room-temperature unsalted butter with 1/2 cup granulated sugar and 1 cup packed light brown sugar on medium-high speed for 2 to 3 minutes until light and fluffy. Scrape the bowl once for even mixing. Add eggs and vanilla: Reduce mixer speed and add two large room-temperature eggs one at a time, mixing until incorporated. Add 1 teaspoon vanilla extract. Mixing slowly prevents over-aeration that can change baking behavior. Incorporate dry ingredients: Add the flour and cocoa mixture in two additions, mixing on low until just combined. Avoid overmixing; stop when you see no streaks of flour. The dough should be firm enough to scoop but pliable. Portion dough: Using a large cookie scoop (approximately 3 tablespoons), portion dough into the prepared muffin tins. Gently press each mound into place so it contacts the pan bottom—this helps create an even cup shape while baking. Bake and form cups: Bake at 350°F for 10 to 13 minutes. The cups should be mostly set at the edges but still soft in the center. Immediately remove from oven and press a small jar or heatproof container into the center of each warm cup to form a well. Press firmly and hold for a few seconds; the warm dough will shape and set as it cools. Cool and release: Let the tins cool for 10 minutes. Loosen each cup slightly by twisting the pan, then let them cool another 5 minutes before removing and transferring to a wire rack to cool completely. Complete cooling prevents the filling from melting when added.

Storage Tips

Store filled cups in an airtight container in the refrigerator for up to 4 days. Place a sheet of parchment between tiers if stacking to protect decorations. For longer storage, freeze baked unfilled cups for up to 3 months; thaw completely at room temperature before filling. If you prepare the filling ahead, keep it chilled in a sealed container for up to 2 days and re-whip briefly before piping if it loses some volume. To reheat unfilled cups for a warm-impression serving, warm gently in a 300°F oven for 3 to 4 minutes, then cool slightly before adding filling.

Ingredient Substitutions

If you don’t have black cocoa, increase Dutch-processed cocoa by 2 tablespoons for color and flavor, though the cups will be lighter. For a dairy-free version, substitute vegan butter and a non-dairy cream cheese and use coconut cream whipped to stiff peaks; flavor and texture will vary slightly and may be softer. To make these nut-free, avoid candy canes with cross-contamination warnings. If you prefer less sugar, reduce granulated sugar in the cookie by 2 tablespoons and the filling sugar by 1 to 2 tablespoons — expect a subtly less tender cookie and a firmer filling.

Serving Suggestions

Serve chilled or at cool room temperature. Garnish each cup with a sprinkle of crushed candy cane, a small mint leaf, or a tiny red gel dot for a festive touch. Pair with strong coffee, espresso, or a peppermint hot chocolate for a coordinated flavor experience. For a party platter, arrange on a bed of fresh evergreen sprigs or serve in mini cupcake liners for easy grab-and-go appeal. These are also excellent plated with a drizzle of warm chocolate ganache for an elegant dessert course.

Cultural Background

Combining chocolate and peppermint is a long-standing holiday tradition in many Western cuisines, evoking classic candy-cane motifs and festive drinks. The idea of cookie cups draws from pastry techniques that use baked dough as edible vessels — reminiscent of tart shells and cookie cups popular in modern patisserie. This particular version mixes American cookie baking traditions with a creamy, mousse-like filling that nods to no-bake cheesecake styles common at holiday gatherings.

Seasonal Adaptations

For winter holidays stick with peppermint and red accents. In summer swap peppermint extract for vanilla or citrus and garnish with fresh berries or lemon zest. For Valentine’s Day use pink color gel and heart-shaped sprinkles; for St. Patrick’s Day try a hint of crème de menthe instead of peppermint for a green hue. Adjust garnishes seasonally — toasted coconut for tropical vibes or chopped toasted hazelnuts for autumnal depth.

Meal Prep Tips

To streamline, bake several pans of the cups and freeze them unfilled. Make the filling the morning of your event and pipe it into thawed cups an hour before serving. Use a piping bag fitted with a round tip for neat, consistent presentation. Label containers with dates and use freezer-safe trays to avoid crush damage. If transporting filled cups, chill solidly and use insulated carriers with ice packs to prevent melting.

These Chocolate Peppermint Cookie Cups are one of those treats that become a small tradition — easy to make, endlessly customizable, and reliably adored. Make a double batch this season and freeze some for unexpected guests; I promise they’ll become part of your holiday routine.