These Pumpkin Pie Cookies combine the cozy autumn flavor and smooth velvety rich texture of pumpkin pie filling with buttery, tender, soft and chewy brown sugar spice cookies. They are so fun to eat and faster to make and bake compared to whole pumpkin pie. I love to make them for Thanksgiving as part of my dessert table.
Make the cookie dough. Combine butter, brown sugar and granulated sugar in a large bowl or the bowl of a stand mixer and mix on medium speed using an electric hand mixer for 1-2 minutes until pale and fluffy. You can also cream the mixture by hand with a large wide spatula.
Scrape down the sides and bottom of the bowl, then add in the egg and vanilla and mix until evenly incorporated.
Combine flour, baking powder, cinnamon, salt and baking soda in a medium bowl and whisk it together to blend evenly. Add this to the butter mixture and fold it in gently until evenly combined and no streaks of flour remain. Place the dough onto a very lightly floured surface and shape it into a log about 11 inches long and wrap it well with plastic wrap or parchment paper. Refrigerate the log for 30 minutes.
When ready to bake, slice the chilled log into 14 portions and roll each one into smooth balls between the palms of your hands. Place them onto prepared baking sheets, spacing them about 3 inches apart. Lightly flour the bottom of a teaspoon measure and press it down gently into the center of each dough ball while using your other hand to hold the sides in place so you get a nice deep divot. Watch the video for a full tutorial. Use your fingertips to reinforce the divot and press together any cracks that form on the sides. You should have a wide hole in the center and about ½ inch border of cookie dough around the edges. Place the cookie sheet in the fridge to chill again for 10-15 minutes.
Make the filling. Combine pumpkin puree, brown sugar, egg, milk or cream, flour and spice in a small bowl and whisk together so it is evenly blended and smooth. Refrigerate this while you make the cookie dough.
Pour about 2 teaspoons of filling into the center of each shaped dough ball to fill the divot right to the top. Bake 3 minutes, then reduce the oven temperature to 350°F and bake for another 10 minutes until nicely browned around the edges and the filling is no longer wobbly. This is options, but I find I still have a bit of filling left after I’ve filled the raw dough balls, so I like to pull the cookies out halfway through the last baking time of 10 minutes (so, after 5 minutes at 350°F) and top them off with a bit more filling so I can get a thicker center, then continue baking until set.
Remove the baking sheet from the oven and allow the cookies to rest on the baking sheet for 5 minutes, then use a thin spatula to transfer the cookies to a cooling rack to cool completely.
Make the whipped cream topping. Combine cream with powdered sugar and whip to medium-stiff peaks using an electric hand mixer. Once the cookies are completely cooled, fill a piping bag fitted with a star tip with cream and pipe a little over each cookies and finish with a sprinkle of cinnamon.