Decadent Chocolate Cherry Thumbprint Cookies: The Ultimate Holiday Treat
Prepare to be enchanted by these Chocolate Cherry Thumbprint Cookies, a delightful and sophisticated twist on the beloved classic thumbprint cookie. Imagine a rich, homemade chocolate cookie, perfectly tender, cradling a pool of velvety dark chocolate ganache, all crowned with a vibrant maraschino cherry. This isn’t just a cookie; it’s a small work of art that tastes as incredible as it looks.
The timeless combination of deep, rich chocolate and sweet, tart cherry creates a flavor symphony that is utterly delectable and undeniably eye-catching. These cookies are absolutely perfect for any festive occasion, from an elegant Valentine’s Day celebration to cheerful holiday gatherings and, of course, a show-stopping addition to your next Christmas cookie exchange. Each bite offers a harmonious balance of flavors and textures, making them truly unforgettable.
Beyond their irresistible taste, maraschino cherries play a crucial role in the presentation, adding a burst of brilliant color that elevates these cookies from simple treats to visually stunning desserts. The sweet, juicy pop of the cherry perfectly complements the intensity of the dark chocolate, creating an experience that is truly “over the top” in the best possible way. Get ready to impress everyone with these gorgeous and gourmet-tasting cookies that are surprisingly simple to make at home!

Looking to expand your holiday baking repertoire? Don’t miss our other fantastic recipes, including classic thumbprint jam cookies, wonderfully soft gingerbread cookies, and cheerfully decorated Christmas sprinkle sugar cookies. Each offers a unique flavor and festive spirit!
Why You’ll Love Making (and Eating!) These Chocolate Cherry Cookies
These aren’t just any cookies; they’re a celebration in every bite! Here’s why these Chocolate Cherry Thumbprint Cookies deserve a prime spot in your baking rotation:
- Elegant Presentation Value: With their rich chocolate base, glossy ganache, and vibrant red cherry, these cookies boast an inherently elegant and festive appearance. They look sophisticated on any dessert platter, making them perfect for special occasions and impressing guests.
- Homemade Goodness, Effortlessly Achieved: While they look intricate, the homemade chocolate cookie dough is straightforward to prepare. You’ll enjoy the superior taste and texture that only a scratch-made cookie can offer, without any complicated techniques.
- A Topping That Truly Stands Out: The combination of a silky dark chocolate ganache filling and a juicy maraschino cherry creates a “thumbprint” that is anything but ordinary. It’s a fun and exciting twist that elevates these cookies far above typical variations, making them unique and memorable.
- Perfect for Any Gathering: Whether it’s an intimate family dinner, a lively party, or a grand holiday event like Christmas, New Year’s, or Valentine’s Day, these cookies are a crowd-pleaser. Their festive look and delightful flavor profile make them suitable for a wide range of celebrations.
- The Ultimate Cookie Swap Recipe: If you participate in cookie exchanges, these Chocolate Cherry Thumbprint Cookies are a guaranteed hit. They’re visually appealing, taste fantastic, and are distinctive enough to make your contribution stand out from the rest. Get ready for compliments and requests for the recipe!

Essential Ingredients for Your Chocolate Cherry Cookies
The quality of your ingredients directly impacts the final taste and texture of your cookies. This section provides detailed notes on each ingredient and offers useful substitution options. For precise measurements, the full list, and comprehensive instructions, please refer to the printable recipe card located at the very end of this post.

- All-Purpose Flour: The backbone of our cookie. For best results, measure your flour accurately. Fluff the flour in its container, then spoon it gently into your measuring cup, leveling off the top with a straight edge. This prevents over-packing, which can lead to dry, dense cookies.
- Milk: Standard dairy milk (whole, 2%, or skim) works perfectly. If you prefer, unsweetened almond milk or other milk replacements can be used without significantly altering the texture or flavor of the cookie dough. Ensure it’s at room temperature for better incorporation.
- Salt: A small but mighty ingredient! Salt balances the sweetness of the cookies and ganache, enhancing the overall chocolate flavor. Don’t skip it!
- Egg: A large egg at room temperature is ideal. Room temperature eggs emulsify better with the butter and sugar, leading to a smoother, more uniform dough and a lighter cookie texture.
- Unsalted Butter: We highly recommend using real, unsalted butter for its superior flavor and texture. Ensure it’s softened to room temperature so it creams easily with the sugar. If you only have salted butter, simply omit the ¼ teaspoon of salt specified in the recipe to avoid making the cookies too salty.
- Granulated Sugar: Provides sweetness and helps create that wonderful crispy-chewy cookie texture.
- Vanilla Extract: Use a good quality pure vanilla extract. It enhances the chocolate and cherry flavors, adding a warm, aromatic depth to the cookies.
- Unsweetened Cocoa Powder: You can use classic unsweetened cocoa powder or dark (Dutch-processed) cocoa powder for this recipe. Dark cocoa powder will yield a richer, darker cookie with a slightly less bitter chocolate flavor. Either choice will result in delicious cookies.
- Heavy Whipping Cream: This is crucial for creating our silky-smooth chocolate ganache topping. The high fat content ensures a stable and decadent ganache. Do not substitute with half-and-half or regular milk for the ganache.
- Dark Chocolate Chips: We’ve opted for dark chocolate chips for the ganache to give it a deep, intense chocolate flavor that beautifully contrasts with the sweet cherry. However, if you prefer a sweeter ganache, semi-sweet chocolate chips are an excellent alternative and will melt just as well.
- Maraschino Cherries: These bright red cherries are the signature topping! Make sure to drain them thoroughly and gently pat them dry with a paper towel before placing them on the cookies. This prevents excess moisture from making your cookies soggy. If your cherries come with stems, be sure to remove them for easier eating and a cleaner look.
How to Craft Your Delicious Chocolate Cherry Thumbprint Cookies
Creating these beautiful cookies is a rewarding process. Follow these detailed steps to achieve perfect results every time:
Step 1: Prepare Your Baking Environment and Dry Ingredients. Begin by preheating your oven to the specified temperature (usually 350°F / 175°C). Line a large baking sheet with parchment paper or a silicone baking mat to prevent sticking and ensure even baking. In a medium bowl, whisk together your all-purpose flour, unsweetened cocoa powder, and salt. Whisking ensures these dry ingredients are well combined and evenly distributed throughout the dough.
Step 2: Cream Butter and Sugar, Then Add Wet Ingredients. In the bowl of a stand mixer fitted with the paddle attachment (or using a hand mixer), cream the softened butter and granulated sugar together on medium speed. Beat until the mixture is light, fluffy, and pale in color. This process incorporates air, which contributes to the cookie’s tender texture. Next, gradually mix in the room temperature egg, vanilla extract, and milk. Continue to beat until all these wet ingredients are fully blended and the mixture is smooth. Remember to scrape down the sides of the bowl as needed to ensure everything is well combined.
Step 3: Combine Wet and Dry Ingredients. With the mixer on low speed, slowly add the prepared dry ingredients (flour, cocoa, salt mixture) to the wet ingredients. Mix just until the flour streaks disappear and a cohesive dough forms. Be careful not to overmix, as overmixing can develop the gluten in the flour, leading to tough cookies.

Step 4: Chill and Bake the Cookie Dough. Once your dough is mixed, cover the bowl tightly with plastic wrap and refrigerate it for at least one hour (or up to 24 hours). Chilling the dough is a crucial step as it firms up the butter, prevents the cookies from spreading too much during baking, and deepens their flavor. After chilling, scoop the dough using a small cookie scoop (about 1 tablespoon) and roll it into smooth balls. Place them about 1 inch apart on your prepared baking sheet. Bake for 10 to 13 minutes, or until the edges are just set but the centers still look slightly soft.
Step 5: Create the Thumbprints and Cool the Cookies. Immediately after removing the cookies from the oven, while they are still warm and pliable, use the back of a rounded teaspoon or your thumb (gently!) to make a hollow indentation in the center of each cookie. Be careful not to press too hard or push all the way through. This creates the perfect little well for our ganache and cherry. Allow the chocolate cookies to cool completely on the baking sheet before proceeding to the next step. Cooling them on the sheet helps them firm up and prevents breakage.
Step 6: Prepare the Ganache and Assemble. While the cookies cool, prepare your rich chocolate ganache. In a microwave-safe bowl, combine your dark chocolate chips, heavy whipping cream, and a tablespoon of butter. Heat in the microwave in 30-second intervals, stirring well after each interval, until the mixture is completely smooth and glossy. Be careful not to overheat. Once the ganache is ready and the cookies are cool, spoon a small amount of the ganache into the hollow center of each cookie. Immediately place one drained and patted-dry maraschino cherry on top of the ganache in each cookie. Allow the ganache to set completely at room temperature or in the refrigerator for about 15-30 minutes before serving. This ensures a neat and firm topping.

Creative Variations to Explore with Your Thumbprint Cookies
One of the best things about thumbprint cookies is their versatility! Feel free to get creative and customize this recipe to your liking with these delicious variations:
- Speedy Cookie Base: If you’re short on time, you can easily swap the homemade chocolate cookie dough with a high-quality chocolate boxed cake mix cookie. Simply follow the “doctoring” instructions on the cake mix box (usually adding an egg and oil) and then proceed with the thumbprint steps.
- Alternative Cherry Fillings: Instead of a whole maraschino cherry, consider filling the center with a dollop of cherry pie filling or a high-quality cherry preserves for a different texture and an intensified cherry flavor. Make sure any preserves are firm enough not to run.
- Different Chocolate Toppings: While our dark chocolate ganache is divine, you can experiment with other luscious chocolate toppings. Try using a ready-made hot fudge sauce, a rich chocolate syrup, or even a creamy chocolate frosting for a quicker finish.
- Explore Other Cookie Flavors: Don’t limit yourself to chocolate! You could use a vanilla-flavored cookie base, an almond-flavored cookie, or even a cherry-flavored cookie dough to create a truly unique thumbprint experience. The possibilities are endless.
- Add a Nutty Crunch: Before baking, you could roll the cookie dough balls in finely chopped nuts like pecans or walnuts for an added layer of flavor and texture.
- Extra Drizzle or Sprinkles: Once the ganache and cherry are set, consider a delicate white chocolate drizzle over the top, or a sprinkle of festive nonpareils for extra visual appeal and a slight crunch.

Expert Tips for Perfect Chocolate Cherry Thumbprint Cookies
Achieving bakery-quality cookies at home is easier than you think with these professional tips:
- Avoid Overbaking at All Costs: This is perhaps the most crucial tip for any cookie recipe. Overbaked cookies will be dry, crumbly, and lack that desirable tender chewiness. Watch for the edges to just set and the centers to still appear slightly soft. They will continue to cook slightly from residual heat once removed from the oven.
- Thoroughly Drain Maraschino Cherries: Excess moisture from the cherries is the enemy of a perfectly set cookie and ganache. Ensure you drain the maraschino cherry juice completely and then gently pat them dry with a paper towel before placing them into the ganache. This prevents soggy cookies and ensures a clean finish.
- Gentle Indentations: When creating the thumbprint in the center of the warm cookies, use a light touch. Whether using a teaspoon or your actual thumb, apply just enough pressure to form a shallow well for the ganache. Pressing too hard can cause the cookies to crack or even break apart.
- Room Temperature Ingredients are Key: For the cookie dough, make sure your butter and egg are at room temperature. This allows them to emulsify properly, creating a smooth, homogenous dough that bakes evenly and results in a better texture.
- Accurate Flour Measurement: As mentioned, properly measuring flour by spooning it into the measuring cup and leveling it off (rather than scooping directly from the bag) prevents adding too much, which can lead to dense, dry cookies.
- Don’t Skip the Chill Time: Chilling the cookie dough is vital. It solidifies the butter, preventing the cookies from spreading too much in the oven, and allows the flavors to meld, resulting in a richer taste and better texture.
- Cool Completely Before Filling: Resist the urge to fill your cookies while they are still warm. The warm cookie will melt your ganache, leading to a messy, unset topping. Patience is a virtue here!

Storage Solutions for Your Chocolate Cherry Cookies
Proper storage ensures your delicious Chocolate Cherry Thumbprint Cookies stay fresh and delightful for as long as possible. Due to the maraschino cherries, which can release moisture and impact freshness, refrigeration is highly recommended for optimal quality.
Once the ganache has completely set, arrange your cookies in an airtight container. Layer them carefully, ideally with parchment paper between layers to prevent them from sticking together or the ganache from smudging. Stored in the refrigerator, these cookies will maintain their freshness and delicious taste for up to 5-7 days. The cool temperature helps preserve the texture of both the cookie and the ganache, and also keeps the cherries at their best.
For longer storage, these cookies freeze beautifully! Simply place the cooled and filled cookies in a single layer on a baking sheet and freeze for about an hour until firm. Then, transfer the frozen cookies to a freezer-safe airtight container or a heavy-duty freezer bag, again, with parchment paper between layers if stacking. They can be frozen for 2-3 months. When you’re ready to enjoy them, thaw the cookies overnight in the refrigerator. If you only want one or two, you can quick-thaw them on the counter at room temperature for approximately one hour. Enjoying them slightly chilled or at room temperature is equally delightful!
More Delicious Homemade Cookies Recipes to Try
- Hidden Hershey Kisses Cookies
- Peanut Butter Cup Cookies
- Rolo Stuffed Cookies
- Red Velvet Cake Mix Cookies
- Air Fryer Chocolate Chip Cookies
- Gingerbread Men Cookies
- Classic Sugar Cookies

Chocolate Cherry Thumbprint Cookies
Author: Jaclyn
Ingredients
- ½ cup butter softened
- ⅔ cup granulated sugar
- 1 large egg room temperature
- 2 Tablespoons milk
- 1 teaspoon vanilla extract
- 1 cup all-purpose flour
- ⅓ cup unsweetened cocoa
- ¼ teaspoon salt
- ¾ cup dark chocolate chips
- ¼ cup heavy whipping cream
- 1 Tablespoon butter
- 24 to 30 stemless maraschino cherries drained and patted dry
Instructions
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Preheat the oven to 350 F. Line a large baking sheet with parchment paper.
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Beat the butter with a hand mixer or stand mixer at medium speed until fluffy. Slowly add the sugar, scraping the bowl down as needed. Add the egg, milk, and vanilla, blending until well mixed.
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Sift together the flour, cocoa, and salt. Add the flour mixture to the butter mixture and beat until combined.
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Cover the dough with plastic wrap and refrigerate for at least one hour.
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Using a small (about 1 tablespoon) cookie scoop, scoop dough onto the cookie sheet, placing the dough about 1 inch apart.
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Bake for 10 to 13 minutes.
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When the cookies are done, remove them from the oven and gently press the back of a teaspoon into the center of each cookie. Allow the cookies to cool on the baking sheet.
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Meanwhile, place the dark chocolate chips, cream, and butter in a microwaveable bowl. Heat in the microwave, stirring every 30 seconds until smooth.
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Spoon a small amount of the chocolate into the hole in each cookie and immediately place a cherry in the center. Allow the chocolate to set completely before serving.
Equipment You’ll Need for Baking Success
Having the right tools can make all the difference in your baking journey. For these Chocolate Cherry Thumbprint Cookies, here’s a list of essential (and helpful) equipment:
- Stand Mixer or Hand Mixer: Crucial for creaming butter and sugar and mixing the dough evenly.
- Large Baking Sheets: To accommodate all your delicious cookies.
- Parchment Paper or Silicone Baking Mats: For non-stick baking and easy cleanup.
- Measuring Cups and Spoons: For accurate ingredient measurements.
- Rubber Spatula: For scraping down the bowl and folding ingredients.
- Small Cookie Scoop (1 tablespoon size): Ensures uniformly sized cookies for even baking.
- Cooling Rack: Allows cookies to cool completely and prevents them from becoming soggy on the bottom.
- Microwave-Safe Bowl: For making the chocolate ganache quickly and efficiently.
- Small Spoon or Teaspoon: To create the indentations in the warm cookies.
- Airtight Containers: For proper storage of your baked cookies.
Troubleshooting Common Cookie Issues
Even experienced bakers encounter a hiccup now and then. Here are some common issues you might face and how to troubleshoot them:
- Cookies Spreading Too Much: If your cookies flatten out excessively, several factors could be at play. Ensure your butter wasn’t too soft (it should be pliable but still hold its shape, not melted). Also, verify you measured your flour correctly and didn’t accidentally use too little. Most importantly, do NOT skip the chilling time! A well-chilled dough is essential for preventing spread. Your oven temperature might also be too low.
- Cookies are Dry and Crumbly: This is almost always a sign of overbaking. Keep a close eye on your cookies in the oven. Remember, they should look slightly soft in the center when you pull them out, as they will continue to set as they cool. Over-measuring flour can also contribute to dry cookies.
- Edges are Cracking when Making Indents: If your cookie edges crack significantly, the dough might be a bit too dry or not fully cooled. Make sure you press gently and create the indent while the cookies are still warm but not hot, allowing for some flexibility.
- Ganache is Too Thin or Too Thick: If your ganache is too thin, it might be too hot or need a bit more chocolate. If it’s too thick, gently warm it again and stir in a tiny bit more warm heavy cream (1 teaspoon at a time) until it reaches your desired consistency.
- Cherries Make Cookies Soggy: As emphasized in the tips, this is due to excess moisture. Always drain and thoroughly pat your maraschino cherries dry before placing them on the ganache.
Nutrition

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