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.
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.
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.
Ingredient Notes
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
- 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.
- 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
- 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.
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.
More Chocolate Cookie Recipes
- Caramel Filled Chocolate Cookies
- Double Chocolate Cookies
- Chewy Chocolate Dipped Oatmeal Cookies
- Chocolate Brownie Oatmeal Cookies
- Chocolate Peppermint Crinkle Cookies
- Check out my entire collection of cookie recipes!
Sign up for my free newsletter for all the latest recipes and join me on Facebook, Instagram and Pinterest for more cooking inspiration!
Chocolate Covered Cherry Cookies
Video
Ingredients
For the Chocolate Thumbprint Cookies
- 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
For the Chocolate Cherry Frosting
- 1 cup semisweet chocolate chips
- ½ cup sweetened condensed milk
- 2 tablespoons reserved maraschino cherry juice, plus additional as needed
Instructions
- Preheat oven to 350 degrees F.
- In a large mixing bowl, use an electric mixer to cream together the butter and sugars until fluffy. Beat in the egg and vanilla.
- In a separate bowl combine the dry ingredients and then add to creamed mixture a little at a time, beating until well combined.
- Using a small cookie scoop and/or your hands, shape the dough into 24 balls, about 1-inch round, and place them on ungreased or parchment paper lined baking sheets. Slightly indent each ball of dough with one of your fingers and then place one maraschino cherry in each indentation.
- Bake for 10 to 11 minutes. Remove from the oven and allow cookies to cool on the baking sheets for about 5 minutes. Transfer cookies to wire racks to cool completely.
Easy Chocolate Cherry Frosting
- Meanwhile, melt chocolate chips and sweetened condensed milk in a small, heavy saucepan over LOW heat, stirring constantly. Remove from the heat, add 2 tablespoons reserved cherry juice, and stir until smooth. Add additional cherry juice, if necessary, to reach the desired consistency.
- Drizzle the frosting over the cooled cookies or alternately, transfer the frosting to a pastry bag fitted with a small circle tip and pipe over the cookies for a more uniform look.
Notes
Nutrition
Nutrition information is automatically calculated using generic ingredients, and is an estimate not a guarantee. For more accurate results, please refer to the labels on your ingredients at home.
More Thumbprint Cookies
Adapted from Better Homes and Gardens
This post was originally published on February 11, 2014. It has been updated with new text and images.
Just wondering if I could use glace cherries instead as its what i have?
I’ve never tried it but would think it should work fine.
This recipe is killer! I am a skilled baker but cookies are always my downfall. For some reason the little buggers just never cooperate with me! This recipe is now the only recipe I ever want to bake because of the quality and taste!
Like another commenter I too did not have enough cherries for the whole batch so I rolled the extra balls in sugar and pressed them down. They were also AMAZING. Next time I think I will try chopping cherries up and adding them to the batter. Who knows, I may even get a little crazy and roll them in powdered sugar next time! The base is very much like a fudgy brownie. WOOF.
All in all, incredibly versatile concept with a FOOL-PROOF base recipe. Thank you!
My daughter is getting married on Sunday. How many days will they keep before wedding? Should they be stored in tuperware container?
You really want them to be fresh and good quality if you’re serving them at a wedding so I would recommend making the no more than two days in advance, storing them unfrosted in an airtight container (Tupperware is fine). I recommend adding the cherries and frosting on the day you serve them for the best result.
Do these cookies freeze well even with the frosting?
I love these cookies I’ve been making these cookies for my family since 1997 they are one of my family’s favorites only the fudge frosting we bake on the top not add after the cookies are baked. Glad to see people still love these cookie after all these years.
I just made these cookies. Followed recipe exactly. Except I put cherries on some and Hershey kisses on a few. ( only because I didn’t have a full jar of cherries) but these cookies came out amazing. I’m a chocolate freak anyway and these are a keeper. They are rich in flavor and soft and chewy.
Chocolate on chocolate… I like the way you think, Jennifer! So glad you love the cookies 🙂
Have you tried adding nuts to the batter?
I haven’t tried it. Let me know if you do!
I increased the amount to 4 dozen cookies. Please clarify how much flour and vanilla should be used. Both show 2-1(?). I used 2-1/2 cups flour and they seemed kind of dry and very chocolatey. Less than 1 C cocoa? What is the correct amount of flour? If you double the 2 dozen recipe, it would be 3 cups flour. Please advise.
Hi Judy. For 4 dozen cookies you are just doubling the recipe so you’ll need 3 cups flour, 3 teaspoons vanilla, and 1 cup unsweetened baking cocoa. My recipe card calculator was a little hung up but I believe it should be working just fine now.
Thanks for sharing! Do they keep long?
Hi Valerie,
I wanted to get back to you and let you know that these cookies froze beautifully!!! I put them in the refrigerator for a couple of hours first, to allow the icing to completely set up (didn’t want them to smudge) and then froze them in a single layer. Took them out and added them to my platter of Christmas cookies on Christmas Eve and they absolutely stole the show! Not only were they beautiful to look at, they were delicious, soft, and so fudgy, everyone loved them!
I did add more cherry juice to both the cookie batter and the icing (only because I wanted a really strong cherry taste) but I know the recipe would have been wonderful either way. And now knowing that they are freezable (a must for me at Christmastime) just puts these cookies completely over the top!
These will be my go-to cookies from now on, any time of the year. Thank you so much for sharing this wonderful recipe, Valerie!!
Thank you for sharing your insight on freezing. That answered my question before I even asked it.
We made these in our culinary club at our Retirement home for Christmas…OMG they were so good and they stayed soft for a couple weeks. We are making again tomorrow. Yum
I just made these and all I can say is “These are the bomb!!!” Wow! I doubled my recipe and cut some of my cherries in half to make sure I had enough. I agree with an earlier comment that it makes plenty of icing, I could have gotten away with not doubling that but I have left overs for dunking something!