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Chocolate Covered Cherry Cookies

5 from 1 vote
These chocolate covered cherry cookies have a soft chocolate cookie base and a thumbprint of chocolate and a maraschino cherry!
Prep Time 10 minutes
Cook Time 8 minutes
Assembly Time 20 minutes
Total Time 38 minutes
Servings: 50 cookies
Course: Dessert
Cuisine: American

Ingredients
  

For the chocolate cookies
  • ¾ cup unsalted butter softened
  • cup light brown sugar packed
  • 2 tablespoons milk
  • 1 egg
  • cup semi-sweet chocolate (melted), 2 ounces
  • 2 cups all-purpose flour
  • ½ cup unsweetened cocoa powder
  • 1 teaspoon baking soda
  • 1 teaspoon salt
For the cookie topping
  • 50 maraschino cherries (stemless)
  • ½ cup semi-sweet chocolate melted, 4 ounces

Equipment

  • Hand or stand mixer
  • medium mixing bowls
  • Measuring cups and spoons
  • piping bag (optional)
  • silicone spatula
  • Cookie sheet

Method
 

To make the chocolate cookies
  1. Preheat oven to 350 degrees (use convection bake if you have it).
  2. Using a stand mixer fitted with the paddle attachment or a hand mixer beat softened butter and brown sugar on high for 1-2 minutes. Scrape down the bowl once complete.
  3. Add in milk, egg, and melted chocolate. Mix until combined. Scrape down the bowl once complete.
  4. In separate bowl, whisk dry ingredients together (flour, cocoa powder, baking soda, salt).
  5. Add dry ingredients to wet ingredients in 2-3 portions. Mix until combined, scrape down the bowl once complete.
  6. Roll the dough into small 1-inch dough balls and place them on a well-greased cookie sheet (you can also line the cookie sheet with parchment paper). Each cookie should be at least 2 inches apart.
  7. Bake for 8-10 minutes or until the top of the cookies just begins to crack.
  8. Remove them from the oven and use a teaspoon measuring spoon to add a 'thumbprint' in each cookie. Do this immediately when they come out of the oven.
To assemble the cookies
  1. Drain the maraschino cherries and pour them onto some paper towels to dab off any excess liquid.
  2. Allow the chocolate cookies to cool to room temperature, then spoon a small amount of chocolate (about ½ a teaspoon) into the thumbprint of about 10 cookies.
  3. Place one maraschino cherry on top of the melted chocolate (the chocolate acts as a 'glue' for the cherry).
  4. Repeat the above steps, spooning the melted chocolate into about 10 cookies at a time, then adding maraschino cherries until you have covered each cookie.
  5. Use the remaining melted chocolate to drizzle over the top of each cookie. Place the chocolate in a piping bag or ziploc bag and cut a very thin tip to drizzle the chocolate for best results.
  6. Allow the chocolate to set, then enjoy!