Name: Chocolate Covered Cherry Cookies
Prep time: 25 min
Cook time: 10 min
Total time: 35 min
Ingredients: ½ cup butter (softened); ½ cup light brown sugar; ½ cup granulated white sugar; 1 egg; 1 ½ teaspoons pure vanilla extract; 1 ½ cups all-purpose flour; ½ cup unsweetened cocoa powder; ¼ teaspoon salt; ¼ teaspoon baking powder; ¼ teaspoon baking soda; 24 maraschino cherries (blotted dry); 1 cup semisweet chocolate chips; ½ cup sweetened condensed milk; 2 tablespoons reserved maraschino cherry juice (plus additional as needed)

If you are a fan of chocolate and cherries you’ve got to try these Chocolate Covered Cherry Cookies. These fudgy, brownie-like thumbprint cookies have a sweet cherry peeking through a drizzle of cherry-infused chocolate frosting.

Chocolate Covered Cherry Cookies on a white plate with maraschino cherries.

These chewy Chocolate Covered Cherry Cookies have such a nostalgic feel for me. Probably due to my fond maraschino cherry memories from childhood but also because all thumbprint cookies hold a special place in my heart.

I had such a thing for maraschino cherries when I was a kid and I blame it all on the Shirley Temple. That beverage was all the rage with the hip 8-year old crowd in the early 70’s and I can remember stuffing about 5 or 6 maraschinos in my glass at a time. Weird kid? Maybe. But my love for maraschino cherries has not dwindled with age.

A close up of a Chocolate Covered Cherry Cookie on a wire rack.

These chewy chocolate cherry cookies are an excellent choice for Valentine’s Day and Christmas. They are bright and cheerful and a great alternative to giving a box of chocolates.

Chocolate cookies with maraschino cherries and frosting on a wire rack.

Ingredient Notes

The ingredients for Chocolate Covered Cherry Cookies with overlay text.

For the Chocolate Thumbprint Cookies

Butter – Let the butter sit at room temperature for an hour or two before beginning. If you forget, microwave it on the defrost setting or 30% power in 5-second increments until it’s softened.
Light brown sugar
Granulated sugar
Egg
Pure vanilla extract
All-purpose flour
Unsweetened cocoa powder – Cocoa powder adds rich chocolate flavor the thumbprint cookie base.
Salt
Baking powder and baking soda
Maraschino cherries – These preserved, sweetened cherries are commonly used in both alcoholic and non-alcoholic beverages and as a garnish on everything from baked hams to ice cream sundaes. You’ll find jars of maraschino cherries in the canned fruit section of your grocery store.

For the Chocolate Cherry Frosting

Semisweet chocolate chips
Sweetened condensed milk –
Maraschino cherry juice – The cherry flavor in the frosting comes from a little of the reserved cherry juice from the jar of maraschino cherries.

How to Make Chocolate Covered Cherry Cookies

Ingredients are mixed in a bowl to make chocolate cookie dough.

Cream together the butter and sugars until fluffy and then beat in the egg and vanilla.
In a separate bowl combine the dry ingredients.
Add the dry ingredients to creamed mixture a little at a time.
Beat the mixture until it is well combined.

A thumb presses into a ball of chocolate cookie dough and an hand places a maraschino cherry on top.

Roll the dough into 1-inch balls (you should have about 24), and place them 2-inches apart on the prepared baking sheet. Use a small cookie scoop to easily create evenly sized cookies.
Place them on an ungreased or parchment paper lined baking sheet. Slightly indent each ball with one of your fingers, smoothing out and reshaping the dough a little, if needed.
Place one maraschino cherry into each indentation in the thumbprint cookies. Bake at 350 degrees for 10 to 11 minutes. After baking, allow the cookies to cool on baking sheets for about 5 minutes then transfer to a wire rack to cool completely.

Blot the maraschino cherries lightly with a paper towel before placing them on the cookie dough. A little juice is okay but you don’t want them dripping wet.

Easy 3-Ingredient Chocolate Cherry Frosting

Cherry chocolate frosting in a sauce pan and being piped over the top of cookies.

Melt the chocolate chips and sweetened condensed milk in a small, heavy saucepan over low heat, stirring constantly. Remove from the heat and add the reserved maraschino cherry juice and stir until smooth. You may need to add a little additional juice to reach the desired drizzling or piping consistency you are after
Use a pastry bag fitted with a small circle tip to pipe the frosting over the completely cooled cookies. Or, just drizzle the frosting over the cookies from the pointed tip of a spoon.

You’ll have about half a can of luscious sweetened condensed milk left over. For an indulgent java experience try Pioneer Woman’s Vietnamese Iced Coffee and there are lots of other great ways to use leftover sweetened condensed milk.

Chocolate cherry cookies with frosting on a wire rack.

Storing Frosted Cookies

I like to store frosted cookies in a single layer in a baking pan with a lid to be sure the frosting stays intact. You can also store the cookies in an air tight container between layers of wax or parchment paper after the frosting has had time to set. Store at room temperature and consume within 3 to 4 days.

Freezing Chocolate Covered Cherry Cookies

For the best quality, I recommend freezing unbaked cookies. Once you form the balls of dough, place them on a baking sheet lined with wax or parchment paper and freeze until firm. Transfer them to a freezer bag or other airtight container and freeze for up to 3 months. When ready to bake, thaw the dough completely in the refrigerator. Once thawed, form the indentations, fill with cherries, and bake and frost as directed in the recipe.

A chocolate cherry cookie with a bite missing.

Chocolate Covered Cherry Cookies

3.68 from 88 votes

Course: Dessert

Cuisine: American

Author: Valerie Brunmeier

Keyword: chocolate covered cherry cookies

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Prep Time:25 minutes

Cook Time:10 minutes

Total Time:35 minutes

Servings: 24 cookies