Christmas Cookies: Chocolate Covered Cherry Cookies

Chocolate Covered Cherry Cookies

These Chocolate Covered Cherry Cookies won’t last long at your next get together. They take a little extra effort, but they’re SO worth it! They’re perfect for Christmas and Valentine’s Day!
Disclosure: This post for Chocolate Covered Cherry Cookies includes affiliate links, this means I make a few cents if you buy the item after clicking my link. This costs you nothing, but it helps keep this blog running on butter…lots of butter!
Course Dessert
Cuisine American
Keyword cherry, chocolate, Cookies, holiday
Prep Time 30 minutes
Cook Time 10 minutes
Total Time 40 minutes
Servings 4 dozen cookies
Calories 89kcal
Author Jillian - a Food, Folks and Fun original!


  • 1 1/2 cups flour
  • 1/2 cup unsweetened dark cocoa powder
  • 1/2 teaspoon salt
  • 1/4 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 cup unsalted butter at room temperature
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon pure vanilla extract
  • 1 teaspoon almond extract
  • 8 ounces semisweet chocolate chips
  • 1/2 cup sweetened condensed milk
  • 2 teaspoons maraschino cherry juice
  • 48 maraschino cherries drained and patted dry


  • MAKE COOKIES: Move oven rack to middle position and preheat oven to 350 degrees F. Line 2 cookie sheets with parchment paper or silicone baking mat, set aside.
  • In a small bowl whisk together flour, cocoa powder, salt, baking powder, and baking soda.
  • In the bowl of stand mixer fitted with paddle attachment, beat butter and sugar together on medium speed until lighter in color and fluffy, about 2-3 minutes. Beat in egg, vanilla extract, and almond extract until combined.
  • Add flour mixture to mixer bowl, and pulse on lowest setting until flour is combined and no flour streaks remain about 30-60 seconds.
  • Shape dough into 1-inch balls and place on prepared cookie sheets about 2 ½ inches apart. Press your thumb about 1/3 of the way down into the center of each dough ball.
  • MAKE FROSTING: In a small saucepan over medium heat, add sweetened condensed milk and chocolate chips and stir frequently until melted. Remove from heat and stir in maraschino cherry juice.
  • BAKE COOKIES: Spoon frosting into the thumbprint of each dough ball, and top with a cherry. Bake for 10-11 minutes. Let cookies cool on cookie sheets for 20 minutes, and then transfer cookies to wire rack to cool completely.


Serving: 1cookie | Calories: 89kcal | Carbohydrates: 14.66g | Protein: 1.25g | Fat: 3.06g | Cholesterol: 8mg | Sodium: 38mg | Potassium: 46mg | Fiber: 0.8g | Sugar: 10.39g | Vitamin A: 150IU | Calcium: 20mg | Iron: 0.5mg