Gourmet Black Cherry Cup Cookies: An Easy, Homemade Recipe for Your Christmas Traditions

Step into the festive season with a delightful twist on a classic holiday treat: our Black Cherry Cup Cookies. These aren’t just any cookies; they’re a sophisticated upgrade to the beloved cherry pie cookie, featuring a luscious homemade black cherry filling infused with warm cinnamon and a hint of rich brandy. Forget the mundane; these gourmet cookies are designed to elevate your Christmas cookie tradition, offering a burst of vibrant flavor and elegant presentation that will impress family and friends alike. Perfect for holiday gatherings, cookie exchanges, or simply enjoying a cozy evening by the fire, these mini pie-like treats combine a tender, flaky cream cheese crust with a deeply flavorful, sweet-tart cherry filling. Prepare to make these exquisite Black Cherry Cup Cookies a cherished part of your annual celebrations for years to come.

This post was first published December 2013 and updated December 2019 for photos and content.

Each December, as the holiday season unfurls its magic, a particular tradition takes center stage in my kitchen: baking Christmas cookies. Among the myriad festive treats, these Black Cherry Cup Cookies are always the first on my list. There’s a profound affection I hold for this recipe, which has been lovingly adapted from an exceptionally old family heirloom. While the original recipe was cherished, I’ve refined it over the years, transforming a simple, comforting cookie into something truly spectacular. This update ensures that the essence of tradition remains, while embracing a fresh, vibrant, and utterly delicious homemade touch that truly sets these cookies apart.

For many years, the classic version of these cookies relied on canned cherry pie filling, which, in its own right, delivered a perfectly pleasant treat. However, my culinary journey led me to experiment with creating my own filling from scratch. This decision was a game-changer. The transformation was immediate and profound, especially when I discovered the unparalleled richness and deep hue of fresh or frozen black cherries. Not only do these black cherries lend an incredibly elegant and sophisticated appearance to each cookie, elevating them to truly gourmet Christmas cookies, but the homemade filling itself is, quite simply, light-years ahead in terms of flavor. The depth of taste, the natural sweetness, and the vibrant cherry essence are incomparable, making every bite a memorable experience.

Key Ingredients for the Perfect Homemade Black Cherry Pie Filling

Crafting the perfect black cherry pie filling from scratch might sound daunting, but it’s surprisingly simple and uses readily available ingredients. The magic truly happens when these components come together to create a rich, vibrant, and perfectly balanced filling that far surpasses any store-bought alternative. Here’s a closer look at what you’ll need:

• Black Cherries: The star of the show! Whether you opt for fresh or frozen (and thawed) black cherries, their deep color and intense flavor are essential. Pitted cherries are key for convenience.
• Lemon Juice: A touch of fresh lemon juice is crucial. It’s not just for flavor; it brightens the cherries and, more importantly, helps to cut through the sweetness, ensuring the filling is perfectly balanced and not cloyingly sweet.
• Granulated Sugar: Essential for sweetening and enhancing the natural fruit flavors. The amount can be adjusted slightly to your preference, depending on the sweetness of your cherries.
• Cornstarch: This acts as our thickening agent, giving the filling that desirable, luscious, and spoonable consistency without being overly gummy.
• Brandy: A splash of brandy adds a wonderful depth and warmth to the filling, complementing the cherries beautifully and giving these cookies their signature gourmet touch. If you prefer to avoid alcohol, you can substitute with a little extra cherry juice or water, though the brandy truly elevates the flavor profile.
• Ground Cinnamon: Just a hint of cinnamon brings a cozy, spiced aroma and flavor that perfectly pairs with black cherries, especially for a Christmas cookie recipe. It adds another layer of warmth without overpowering the fruit.
• Kosher Salt: A tiny pinch of salt might seem unexpected in a sweet recipe, but it’s a secret weapon! It enhances all the other flavors, making the cherries taste even more vibrant and the filling more complex.

As you can see, these are all standard kitchen staples, easily sourced and quickly combined in a saucepan to create an extraordinarily flavorful and aromatic filling that will make your Black Cherry Cup Cookies truly unforgettable.

Simple Steps to Bake Irresistible Black Cherry Cup Cookies

Creating these delightful Black Cherry Cup Cookies is a straightforward process, broken down into a few manageable steps. Even if you’re new to baking, you’ll find this recipe approachable and incredibly rewarding. Here’s an overview of the journey from ingredients to oven-fresh treats:

1. Prepare the Cream Cheese Cookie Dough: The foundation of these cookies is a wonderfully tender and rich cream cheese crust. You’ll begin by combining just three simple ingredients – softened cream cheese, unsalted butter, and all-purpose flour – until a smooth, pliable dough forms. This dough is incredibly easy to work with and provides the perfect backdrop for our vibrant cherry filling.
2. Form the Mini Pie Shells: Once the dough is ready, you’ll divide it into small, uniform balls. These balls are then pressed into the cups of a mini muffin tin to create delicate, individual cookie shells. This step is surprisingly quick, especially with the right tool (more on that in our tips section!), ensuring a perfectly shaped base for each treat.
3. Craft the Homemade Black Cherry Filling: While the dough chills briefly or as you form the shells, you’ll whip up the star of the show – the homemade black cherry filling. This luscious concoction comes together in a saucepan in mere minutes, requiring just a gentle simmer and occasional stirring to achieve its perfect, thick consistency. The aroma alone will have your kitchen smelling heavenly!
4. Assemble, Fill, and Bake: With your cookie shells formed and your cherry filling prepared, it’s time for assembly. Each dough-lined cup is generously filled with the warm, fruity goodness. Then, the mini tarts are baked to golden perfection, transforming into elegant, bite-sized delights. A final dusting of powdered sugar after cooling adds a touch of charm and sweetness.

This streamlined process ensures that you can enjoy these easy black cherry cookies without any unnecessary stress, making them an ideal choice for busy holiday bakers or anyone looking for a gourmet treat with minimal fuss.

Expert Tips for Baking Perfect Black Cherry Cup Cookies

Achieving bakery-quality Black Cherry Cup Cookies at home is easier than you think, especially with a few insider tips. These pointers will help ensure your cookies turn out perfectly every time, from forming the crust to getting that luscious filling just right:

• The Mini Dough Tamper is Your Best Friend: While not strictly essential (as we’ll discuss), a mini dough tamper (like the one shown in the photos) is an absolute game-changer for forming the little pie shells quickly and uniformly. Simply take a small ball of dough, place it in the mini muffin cup, and press down with the tamper. For best results and to prevent sticking, lightly flour the tamper between each cup. This small, inexpensive gadget can be found easily online and is a worthwhile investment for any baker, even those who, like me, usually shy away from excessive kitchen tools.
• No Tamper? No Problem!: Don’t fret if you don’t have a tamper. The original family recipe, which has delighted generations, was made long before such gadgets were common. Your fingers work just as effectively! Simply press the dough balls into the muffin cups with your thumb or fingertips, working from the center outwards to create an even shell. The slight imperfection adds a charming, rustic, homemade touch.
• Effortless Removal from Muffin Tins: To ensure your baked cookies pop out of the tins without a hitch, aim to have the cream cheese crust extend slightly up and over the edge of the muffin cup rather than being flush with or below it. This slight overhang provides a lip that makes extraction much easier. Once the cookies have cooled for a few minutes in the tin (they’ll firm up a bit), use a thin butter knife or offset spatula to gently loosen the edges. Carefully lift each cookie out, and transfer them to a wire rack to cool completely.
• Vigilance is Key with the Cherry Filling: The homemade black cherry pie filling comes together very quickly on the stovetop, which means it also has a tendency to scorch if left unattended. It’s crucial to “babysit” the filling while it simmers, stirring it frequently and gently for the recommended 5 minutes or until it thickens to a gel-like consistency. A single moment of distraction could lead to a burned batch, and nobody wants that! Trust me, it’s worth the continuous stir to ensure a perfectly smooth and flavorful filling.
• Don’t Overfill the Cups: When adding the cherry filling to your prepared crusts, resist the temptation to overfill them. The filling will bubble and expand slightly during baking, and an overfilled cup can lead to sticky spills in your muffin tin. Aim for about three-quarters full. The exact number of cherries per cup will vary depending on their size, so focus on the overall volume of filling.
• Cool Completely for Best Texture: While it’s tempting to dive into these warm from the oven, allowing them to cool completely on a wire rack is important. This not only allows the filling to set properly but also ensures the crust achieves its optimal flaky texture. Once cooled, a delicate dusting of powdered sugar adds the perfect finish.

Frequently Asked Questions About Black Cherry Cup Cookies

Here are some common questions and helpful answers to ensure your Black Cherry Cup Cookie baking experience is as smooth and enjoyable as possible:

• Is a mini dough tamper an absolute requirement for this recipe?
  No, not at all! While I highly recommend a mini dough tamper for its efficiency in creating uniform pie shells, it is by no means essential. Our family made these delicious cherry cup cookies for many years, delighting in every bite, long before such a gadget entered our kitchen. Your fingers are perfectly capable tools for pressing the dough into the mini muffin cups. Just use your thumb or fingertips to gently spread and shape the dough evenly against the bottom and sides of each cup. The result will be equally delicious, perhaps with a charming, rustic touch!
• Can Black Cherry Cup Cookies be frozen for later enjoyment?
  Absolutely, and it’s a practice I highly recommend! These cookies freeze beautifully, making them ideal for meal prep, holiday gifting, or simply ensuring you always have a gourmet treat on hand. At room temperature, these delicate cookies typically maintain their optimal freshness for about 4-5 days. Freezing extends their shelf life significantly, allowing you to savor them for up to two months.
• What’s the best method for storing these delicious cookies?
  For optimal freshness, whether at room temperature or in the freezer, I suggest storing these Black Cherry Cup Cookies in a single layer within airtight containers or large ziploc bags. If you’re freezing a larger batch, arranging them in a single layer in a bag allows you to stack multiple bags in your freezer without damaging the cookies. This method also makes it incredibly convenient to grab just a single bag whenever a craving strikes, without having to disturb or thaw the entire batch. Just remember to allow them to come to room temperature or warm them slightly before serving if frozen.
• Is it possible to double or even triple this recipe for a larger yield?
  Yes, and I wholeheartedly encourage it! This homemade cherry cookie recipe is perfectly scalable. In fact, doubling or tripling the recipe is a fantastic idea, especially during the holiday season. These Black Cherry Cup Cookies are the quintessential treat you’ll want to keep a generous stash of at home (and in the freezer!) for unexpected guests or personal indulgence. They also make exquisite, much-appreciated gifts for friends, family, neighbors, and coworkers. Preparing a larger batch ensures you have enough to share the joy without running out yourself!
• Can I use other types of cherries or fruit for the filling?
  While black cherries offer a distinct depth and color that makes these cookies particularly special, you can certainly experiment with other fruits. Red tart cherries are a classic choice and would work well, though they might yield a slightly different flavor profile. For an alternative, consider other small berries like raspberries or blueberries, adjusting the sugar and lemon juice to taste, as their sweetness levels vary. The key is to ensure the fruit is pitted (if necessary) and the filling reaches the right consistency.
• How do I know when the cookies are perfectly baked?
  The baking time for these Black Cherry Cup Cookies is typically 25-30 minutes at 350°F (175°C). You’ll know they are done when the edges of the cream cheese crust are lightly golden brown and the cherry filling appears set and slightly bubbly. Avoid overbaking, as this can lead to a dry crust. Once removed from the oven, the filling will continue to set as the cookies cool.

HERE ARE MORE CHRISTMAS RECIPE IDEAS:

• Christmas Soup – This slow cooker, creamy tomato basil soup is a family tradition.
• Christmas Croissant Breakfast Casserole – Make a day ahead, then bake in the morning.
• Christmas Cranberry Meatballs – These TASTY meatballs are party ready when you are.
• Potato Chip Cookies – Another family heirloom recipe that is ALWAYS a huge hit.
• Scallion Olive Party Dip Cheese Wreath – Wow them all with this perfect cracker spread made into an impressive cheese wreath.

Be sure to also check out my most popular cookie recipe, Potato Chip Cookies.