Old-Fashioned Chocolate Cherry Thumbprint Cookie Recipe

A Chocolate cherry thumbprint cookie recipe is the perfect treat to add a festive touch to your holiday baking! These little cookies have a rich chocolate base with a sweet cherry filling that brings a pop of color and flavor.

Each one has a thumbprint-sized dip in the center, filled with cherry goodness that pairs beautifully with the chocolate. Not only are they delicious, but they’re also simple to make and look amazing on any holiday dessert table.

Jump to Recipe

I spent a lot of time with my Memaw growing up. She was right next door, so my brothers and I basically lived at her house. She was a fantastic cook and baker. After becoming a young widow, she baked to earn extra money. She was one of the hardest working and generous women I’ve ever known.

As a little girl I would sit on her Formica counter in her tiny kitchen, and watch her bake. I still vividly remember the way she measured flour. The perfectly smooth, leveled flour was begging for me to stick my fingers in it. She would let me lick the spatula and beaters when she was finished. I’ve since passed this love of cake batter on to my crew.

I have her handwritten thumbprint cookie recipe in my book. They take me back to Christmas with her. These retro cookies make me want to hang tinsel on my tree, mix up a poinsettia cocktail, and break out Bing Crosby on the record player.

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Making the The Chocolate Cherry Thumbprint Cookie Recipe

1. Start by letting the eggs and butter come to room temperature. Sift together 1 ½ cups of flour, ¼ tsp of salt, and 1 tsp of baking powder in a separate bowl.
2. In the large bowl of an electric mixer beat 2/3 cup of butter, ¾ cup of sugar and 2 eggs until smooth, or about 3 minutes. Stir in 1 tsp of vanilla flavoring.

3. Melt 1 cup semi-sweet chocolate chips in a double boiler. Be careful not to scorch the chocolate.
4. Mix the melted chocolate with the butter, sugar, and eggs. When everything is combined, slowly add in 2 cups of dry ingredients. Let the dough chill in the fridge for at lest 1 hour.

5. In the mean time, rinse and drain two 10oz jars of Maraschino cherries. Pat dry with a paper towel.
6. After the dough has chilled, shape it into 1 inch balls, and place them 2” apart on a parchment paper lined cookie sheet. Press down the center of the cookie with your thumb, and place a Maraschino cherry in the center of each of them.

7. Preheat the oven to 350°F. Bake the chocolate cookies for 10-12 minutes, or until they are set.  Removed cookies from the oven and let them cool completely on a rack.
8. After the cookies have completely cooled, melt remaining 1 cup of chocolate chips in a double boiler, and drizzle chocolate over the tops of the cookies. Let the chocolate set before serving.

Helpful Tips for Making Thumbprint Cookies

• Chill the dough: It’s easier to shape the cookies if the dough is chilled. It helps them hold their shape better when baking.
• Make a deep thumbprint: Use your thumb or the back of a spoon to press a nice dip in the middle of each cookie for the cherry filling.
• Use a cookie scoop: This helps to make sure all your cookies are the same size and bake evenly.
• Don’t overbake: Keep an eye on your cookies and take them out when the edges are just set. They’ll continue to firm up as they cool.
• Store properly: Once cooled, keep your cookies fresh by storing them in an airtight container.
• Add the filling last: Wait until the cookies have cooled a bit before adding the cherry filling to make sure it stays put.

Chocolate Cherry Thumbprint Cookie Recipe FAQs

Can I use melted chocolate for the dough?

No need! These cookies get their rich chocolate flavor from cocoa powder, so no melted chocolate is required. It keeps things simple and mess-free!

Why is my dough too sticky?

If your dough feels sticky, it might be because of the wet ingredients. Try chilling the dough for 30 minutes to make it easier to handle.

How do I get the perfect cookie shape?

Use a small cookie scoop to make sure each cookie is the same size, and don’t forget to press a nice thumbprint in the middle for the cherry filling.

Can I make these cookies ahead of time?

Absolutely! They’re one of those easy recipes that you can bake ahead and store in an airtight container for a few days.

What if I don’t have cherry filling?

No problem! You can use jam, preserves, or even a small piece of chocolate in the middle. Get creative!

Final Thoughts

Chocolate cherry thumbprint cookies are the perfect mix of rich chocolate and sweet cherry flavor, making them a must-have for any holiday cookie tray. They’re easy to make, look festive, and taste amazing. Whether you’re sharing them with family, giving them as gifts, or just enjoying a few yourself, these cookies are sure to be a hit this holiday season.

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