Pumpkin Cannoli Cookie Cups

If you're looking for a dessert that truly captures the essence of fall, these Pumpkin Cannoli Cookie Cups will do just that. The warm, cozy flavors of cinnamon, ginger, and cloves mixed with the creamy, sweet pumpkin filling create a treat that's both comforting and delicious. These cookie cups are perfect for any gathering, from casual get-togethers to Thanksgiving dinner, and they’re a great way to impress your friends and family with a fun twist on traditional cannoli.

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I’ve always loved how simple ingredients can come together to make something extraordinary, and these pumpkin cannoli cookie cups are a prime example. They’re incredibly easy to make and offer a festive pop of flavor in every bite. What’s even better is how they look on a platter, ready to be devoured by anyone who craves something sweet and seasonal. Trust me, once you try these, they’ll become a fall favorite.

A Cozy Fall Treat

These Pumpkin Cannolli Cookie Cups are the perfect dessert for those chilly fall evenings when you’re craving something warm and comforting. With the flavors of pumpkin and cinnamon filling the air, they’ll remind you of cozy nights by the fireplace, surrounded by loved ones. Plus, they’re incredibly easy to make, no complicated steps, just a lot of love and a few simple ingredients.

Ingredients

For the cannoli cups:

• unsalted butter, softened
• granulated sugar
• egg
• molasses
• vanilla extract
• all-purpose flour
• baking soda
• ground cinnamon
• ground ginger
• ground cloves

For the pumpkin cannoli filling:

• cream cheese, softened
• pumpkin purée
• ricotta cheese
• heavy cream
• powdered sugar
• nutmeg
• cinnamon
• ginger
• vanilla extract

For Whipped Topping:

• heavy cream
• powdered sugar
• 1 T bourbon (or vanilla)

How to Make Pumpkin Cannoli Cookie Cups

Start by creaming together the softened butter and granulated sugar in a large mixing bowl. Using a wooden spoon or a hand mixer makes this step easy and ensures everything gets well combined. This is where the base of the cookie dough begins to form. Once the butter and sugar are fluffy and smooth, add the egg, molasses, and vanilla extract. Mix everything together until you get a smooth, silky dough. The molasses gives the dough a rich, deep flavor that pairs perfectly with the spices.

Now, it's time to bring in the dry ingredients. Slowly add in the all-purpose flour, baking soda, cinnamon, ginger, and cloves. I like to use a silicone spatula for this because it helps fold the dry ingredients into the wet mixture without over-mixing. Scrape down the sides of the bowl as you go, ensuring all the ingredients are incorporated. The dough should come together soft but firm enough to scoop and shape.

Next, lightly spray a mini muffin pan with nonstick spray to prevent the cookie cups from sticking. Then, scoop the dough into each muffin cavity, filling each about ⅔ full. I find using a small cookie scoop is the perfect way to get evenly sized dough balls, about 1 inch in diameter. Bake the cookie cups in a preheated oven at 350°F for 10-12 minutes. The edges should be set, and the centers should no longer look raw. Once they’re done, remove them from the oven and allow them to cool slightly in the pan.

While the cookies are still warm, immediately press the center of each cookie with the back of a spoon or a tart shaper. This step is crucial for creating the little wells in the center of each cookie that will hold the pumpkin cannoli filling. Be gentle but firm. Allow the cookies to cool completely in the pan before carefully removing them. This gives the cups time to firm up and ensures they hold their shape when removed.

In a mixing bowl, beat together the softened cream cheese, pumpkin purée, ricotta cheese, heavy cream, powdered sugar, nutmeg, cinnamon, ginger, and vanilla extract until the mixture is smooth and creamy. I recommend using a hand mixer for this step, as it blends the ingredients quickly and evenly, creating a perfect filling consistency. Taste the filling as you go to make sure the spices are balanced to your liking.

Once your cookie cups have cooled completely, it’s time to fill them with the creamy pumpkin mixture. You can use a piping bag or a simple spoon for this step. If you're using a piping bag, fill it with the pumpkin filling and pipe it into each cup, ensuring you fill them generously. If you prefer, a spoon works just as well to scoop the filling directly into the wells. Either way, make sure each cookie cup is overflowing with that rich, creamy filling.

In another mixing bowl, beat the heavy cream with the powdered sugar and bourbon (or vanilla) until stiff peaks form. I recommend using a stand mixer or electric hand mixer for this. The cold heavy cream and powdered sugar will whip up beautifully, giving you a light, fluffy topping. The bourbon adds a subtle depth of flavor, but you can easily swap it for vanilla extract if you prefer. Keep an eye on the mixture to make sure you don’t overwhip it.

Once your whipped cream is ready, pipe a swirl of it onto each filled cookie cup for that extra bit of indulgence. You can use a piping bag or simply dollop the cream with a spoon if you prefer a rustic look. For a final touch, lightly sprinkle each cup with a pinch of cinnamon or nutmeg. This will add a little extra spice and a nice decorative finish. These little treats are best served chilled, so be sure to store them in the fridge until you’re ready to serve.

Serving Suggestions

These pumpkin cannoli cookie cups are perfect for a fall dessert spread. Serve them at your Thanksgiving dinner, a cozy family gathering, or as a sweet treat after a brisk autumn walk. Pair them with a warm cup of chai tea or spiced coffee to really elevate the seasonal flavors. They’re also a hit for potlucks or office parties, where everyone will appreciate the creative twist on a classic.

Storage Tips

To keep these delicious cookie cups fresh, store them in an airtight container in the refrigerator for up to 4 days. However, note that the filling will soften the cookie cups over time, so they’re best enjoyed within a couple of days after making them. If you need to prepare them in advance, feel free to make the cookie cups and filling separately, then assemble them closer to serving time.

More Recipes You’ll Love

If you love these pumpkin cannoli cookie cups, you’re going to adore these other fall-inspired treats. Try my Pumpkin Whoopie Pies, which offer a delightful combination of soft, cake-like cookies with a creamy filling. For a cozy, sweet treat, indulge in Caramel Apple Cheesecake Bars, combining rich caramel and tangy cheesecake in every bite. Another must-try is the Pumpkin Cinnamon Rolls, which will fill your home with the heavenly aroma of cinnamon and pumpkin, perfect for any fall gathering.