This is one of those treats that arrives at a gathering and disappears in minutes. I first made these cherry chocolate cookies on a blustery December afternoon when I wanted something that tasted like a chocolate-covered cherry but in a more comforting, shareable form. They combine deep cocoa cookie dough with a sweet-tart cherry center and a glossy chocolate drizzle. From the first bite you get a tender chocolate crumb, a little pop of cherry jammy filling, and a final silky chocolate note that pulls everything together. Friends immediately asked for the recipe, and the bowl-cleaning that followed convinced me this recipe was a keeper.

My family now requests these for cookie exchanges and small holiday gatherings. I discovered the balance of texture by accident: the dough must be thick enough to hold a small well, but soft enough to bake with a tender edge and slightly chewy center. The cherry filling adds an indulgent, jammy surprise in each cookie while mini chocolate chips dispersed through the dough create little pockets of melted chocolate. These are a dessert you can make in 25 minutes active time and share immediately or stash in the freezer for a later sweet craving.

Ingredients

• Unsalted butter (1/2 cup, softened): Use good-quality butter such as Plugra or Kerrygold if you want a richer flavor; room temperature butter creams more smoothly into the sugars and creates a tender texture.
• Granulated sugar (3/4 cup) and brown sugar (3/4 cup): A combination of both gives caramel notes from the brown sugar and crispness from the granulated; use light brown sugar for a milder molasses flavor.
• Eggs (2 large): Bring eggs to room temperature for better emulsion and slightly lighter cookies; beat in one at a time to ensure good incorporation.
• Pure vanilla extract (2 teaspoons): Adds aromatic warmth; a pure vanilla is preferable over imitation for depth of flavor.
• Unbleached all-purpose flour (2 1/2 cups): Provides structure; spoon into the measuring cup and level off for accurate measurement to avoid dry dough.
• Unsweetened cocoa powder (1/2 cup): Use Dutch-processed for a deeper chocolate color and smoother flavor, or natural cocoa for brighter, slightly acidic notes.
• Baking powder (1 1/2 teaspoons) and salt (1/2 teaspoon): Baking powder gives a gentle lift while salt balances the sweetness—use kosher or fine sea salt for best results.
• Semi-sweet mini chocolate chips (1 cup): Mini chips spread more evenly through the dough and melt into small pockets; Ghirardelli or Nestle Toll House minis are great choices.
• Cherry pie filling (10 ounces): Look for a brand with whole or halved cherries and thick syrup—this keeps the center intact while baking; reserve a small spoon for filling wells.
• Chocolate almond bark (6 ounces): Melts smoothly for drizzling; if you prefer, use a quality chocolate melting wafer or chopped bittersweet chocolate for a less sweet finish.

Instructions

Preheat and prepare: Preheat the oven to 350°F and line baking sheets with parchment paper. Having parchment ready prevents sticking and allows even baking under the cookies' edges. Position racks in the center for the most even heat. Cream butter and sugars: In a large mixing bowl, beat 1/2 cup softened unsalted butter with 3/4 cup granulated sugar and 3/4 cup brown sugar until light and slightly fluffy, about 2 to 3 minutes on medium speed. Properly creamed butter traps air which helps the cookies rise and gives a tender crumb. Add eggs and vanilla: Beat in 2 large eggs, one at a time, ensuring each is fully incorporated before adding the next. Stir in 2 teaspoons pure vanilla extract. The eggs add moisture and structure—too much mixing after adding flour will toughen the dough. Combine dry ingredients: Whisk together 2 1/2 cups unbleached flour, 1/2 cup unsweetened cocoa powder, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt. Sifting is optional but helps avoid cocoa lumps and distributes leavening evenly. Mix dough: Gently fold the dry ingredients into the wet mixture. The dough will be thick and slightly crumbly at first; use your hands if necessary to bring it together without overworking. Overmixing develops gluten and will make cookies tough. Fold in chips: Stir in 1 cup semi-sweet mini chocolate chips until evenly distributed. The mini chips create small bursts of melted chocolate inside the baked cookie. Portion cookies: Using a 1 tablespoon cookie scoop, portion dough into balls and place them about 1 inch apart on the prepared baking sheet. Press each ball lightly and use the back of a large spoon or spatula to create a small well in the center for the cherry filling. Fill centers: Place a small spoonful of cherry pie filling into each well—about 1/2 teaspoon per cookie. Try to keep the filling centered so it doesn’t overflow while baking. Bake: Bake at 350°F for 10 to 11 minutes, until cookies look set but still slightly soft in the center. They will continue to firm on the sheet; avoid overbaking to keep centers tender. Cool and drizzle: Remove from oven and cool on the sheet for 10 minutes. Meanwhile, melt 6 ounces chocolate almond bark in a microwave-safe bowl in 20 to 30 second intervals, stirring until smooth. Drizzle the melted bark over cooled cookies, then transfer to a rack to cool completely.

Storage Tips

Store cooled cookies in an airtight container at room temperature for up to five days. To keep them from sticking, separate layers with parchment or wax paper. For longer storage, wrap each cookie individually in plastic wrap and freeze in a sealed container for up to three months. To reheat from frozen, unwrap and warm gently at 300°F for 5 to 7 minutes or let sit at room temperature for 30 minutes to soften; avoid direct high heat which can harden the filling.

Ingredient Substitutions

If you need to swap ingredients: replace butter with an equal amount of plant-based stick butter for a dairy-free version, though texture will vary slightly. For a gluten-free option, use a 1:1 gluten-free flour blend and add 1/4 teaspoon xanthan gum if the blend lacks it. Use chopped dark chocolate in place of almond bark for a less sweet drizzle, or swap cherry pie filling for cherry preserves if you prefer thicker filling—use the same volume but reduce syrup if very runny.

Serving Suggestions

Serve these on a dessert platter with powdered sugar-dusted cookies for contrast, or alongside vanilla ice cream for an indulgent pairing. Garnish with a few toasted almond slivers or a light dusting of cocoa on the platter. These are excellent for cookie exchanges, bridal showers, or as a sweet finish to a cozy dinner party—serve warm or at room temperature.

Cultural Background

The flavor marriage of chocolate and cherry has roots in classic European confectionery—most famously chocolate-covered cherries. Over time, home bakers adapted the concept into many forms: cakes, cookies, and small candies. These cookies channel that tradition into American holiday baking culture where jam-filled cookies and chocolate-drizzled cookies are beloved. This version is a direct nod to the nostalgic treat while remaining practical for modern baking.

Seasonal Adaptations

In winter, opt for darker chocolate and a splash of cherry liqueur mixed into the filling for an adult twist. For summer, use fresh cherry compote (reduced and slightly thickened) in place of canned filling, and finish cookies with white chocolate drizzle for a lighter look. Swap cocoa for a cinnamon-chocolate blend for autumnal warmth.

Success Stories

Readers often tell me these were the hit of their cookie exchange or the first cookie to vanish at a bake sale. One reader shared that adding 1/8 teaspoon of coconut oil to the melted almond bark kept the drizzle pliable for longer—handy when you must finish a batch between interruptions. Another mentioned using a piping bag for neater drizzling, a tip I now use for gifting batches.

Meal Prep Tips

For efficient assembly, portion the dough into tablespoon-sized balls and freeze on a sheet pan. Once frozen, transfer to a bag and bake straight from frozen, adding an extra 1 to 2 minutes to baking time. Prepare the cherry filling in a small squeeze bottle or piping bag to fill wells quickly and cleanly. Label containers with dates when freezing to maintain quality control.

These cookies are an easy way to make an everyday moment feel special. Try them with your favorite chocolate and a little decorator’s sugar on top—the combination of texture, color, and nostalgic flavor will have family and friends asking for the recipe every time.