Pumpkin Pie Cookies

Closeup of a Pumpkin Pie Cookie with a bite missing on a small fluted plate with cinnamon sticks in the foreground and more cookies in the background.

These Pumpkin Pie Cookies are cinnamon sugar cookie cups filled with pumpkin filling and topped with whipped cream! These bite-sized gems are irresistible!

Course Dessert

Cuisine Cookies

Prep Time 30

Cook Time 20

Total Time 50

Servings cookies

Calories 131kcal

Author Amee

Equipment

Ingredients

Cinnamon Sugar Cookie Cups

2 cups all-purpose flour
1 ½ teaspoons ground cinnamon
¼ teaspoon salt
¾ cup unsalted butter, softened
1 cup granulated sugar
1 egg, at room temperature
1 teaspoon vanilla bean paste (see note)

Pumpkin Filling

1 cup pumpkin purée (see note)
⅓ cup sweetened condensed milk
1 egg
½ teaspoon ground cinnamon (see note on spices)
¼ teaspoon ground ginger
¼ teaspoon ground nutmeg
⅛ teaspoon ground cloves
¼ teaspoon salt

Whipped Cream

½ cup heavy (whipping) cream, cold
4 teaspoons powdered sugar
½ teaspoon vanilla bean paste (see note)

US Customary - Metric

Instructions

Cookie Cups

Preheat oven to 350℉. Grease mini muffin pan and set aside.
In a small bowl, combine dry ingredients (flour, cinnamon, and salt). Set aside.
In the bowl of a stand mixer, combine butter and sugar, beating until light and fluffy. Scrape down the sides of the bowl as needed.
Add egg and vanilla bean paste (see note). Mix to combine. Gradually add the dry ingredients and mix until just combined.
Using a medium cookie scoop (see note), portion about 1.5 tablespoons of dough into each cup of your prepared mini muffin pan. The recipe makes about 30 cookies, so you may have to bake in batches (the pan I used only has 24 mini muffin cups).
Press the cookie dough into the bottom and up the sides of each mini muffin cup. I pressed a shot glass into the center of each to accomplish this. The dough will stick to the shot glass, but dipping the bottom of the glass in sugar will keep it from sticking.

Pumpkin Filling

In a medium bowl, whisk together all the filling ingredients until well incorporated and smooth.
Bake the cookie cups for 10 minutes, then remove from the oven. If the cookies have risen and there isn't much room for the filling, use a measuring spoon to push down the centers a bit. Fill each cookie cup with the pumpkin filling, almost to the top.
Return the cookies to the oven and bake another 10-15 minutes. I've found that some mini muffin pans are smaller or larger than others, so just keep an eye on them to make sure they're not getting overdone!
Allow the cookies to cool in the pan on a wire rack. To remove, I've found that giving each cookie a gentle twist will ensure it's released from the pan.

Whipped Cream

Combine all whipped cream ingredients in the bowl of a stand mixer fitted with the whisk attachment. Start the mixer on low speed, and gradually increase the speed to high. Whip until the cream thickens and forms peaks. Pipe or dollop on top of the cookies as desired.
Store the cookies in an airtight container in the refrigerator for up to one week. For longer storage, you can freeze the cookies (without the whipped cream!) for up to three months.
Enjoy!

Notes

Note on mini muffin pan - I used a mini muffin pan instead of a standard-sized muffin pan because I wanted to cookies to be small and bite-sized. I've found some variability in the sizes of mini muffin pans, so keep an eye on them as they bake to make sure they're not getting overdone! The link I've provided shows you exactly the pan I used.

Note on vanilla bean paste - I love adding vanilla bean paste both for its lovely flavor and the beautiful flecks of vanilla bean it leaves in the cookies and the whipped cream! That said, if you'd prefer to substitute you can use an equal measure of vanilla extract.

Note on cookie scoop: I use a medium cookie scoop to portion out the cookie dough. This helps me to keep them more uniform in size and to keep my hands clean. If you're using a spoon, you'll want about 1.5 tablespoons of dough for each cookie cup.

Note on pumpkin purée - Note that you want pumpkin purée and NOT pumpkin pie filling (sometimes labeled "pumpkin pie mix"), which already has sugar and spices added.

Note on spices - For classic pumpkin pie flavor, I used ground cinnamon, ginger, nutmeg, and cloves in the pumpkin filling. If you prefer, you can substitute with 1 teaspoon of pumpkin pie spice.

Nutrition