Description

Thick and chewy well-spiced Pumpkin Pie Cookies with a crisp bottom and smooth, silky pumpkin pie filling. These large cookies boast a warm pumpkin spice flavor in both the cookie dough and filling, creating the perfect handheld treat for fall and holiday gatherings. Finished optionally with whipped cream, they combine the best elements of pumpkin pie and cookies in one delightful bite.

Ingredients

Scale

For the Cookie Dough:

2 ⅔ cups all-purpose flour (337g)
1 tablespoon pumpkin spice
½ teaspoon salt
3 oz cream cheese, room temperature (86g)
12 tablespoons unsalted butter, room temperature (6oz)
½ cup granulated sugar (110g)
½ cup packed brown sugar (112g)
1 large egg yolk, room temperature
1 teaspoon vanilla extract
⅓ cup coarse sugar for rolling (78g)

For the Pumpkin Pie Filling:

1 large egg, room temperature
¼ cup brown sugar (56g)
Pinch table salt
½ teaspoon pumpkin spice
¼ cup whole milk (2oz)
½ cup pumpkin puree (122g)
¼ teaspoon vanilla extract

For Serving (Optional):

Whipped cream or Cool Whip

Instructions

Preheat Oven and Prepare Baking Sheet: Preheat your oven to 350℉ (177℃). Line a cookie sheet with parchment paper and set aside to prevent sticking and ensure even baking.
Prepare the Cookie Dough: In a medium bowl, whisk together the all-purpose flour, pumpkin spice, and salt. In a large mixing bowl, beat the room temperature cream cheese, unsalted butter, granulated sugar, and brown sugar on medium-high speed until fluffy, about 3 minutes. Scrape down the bowl sides and blend again. Add the egg yolk and vanilla extract, mixing until incorporated. Gradually add the flour mixture in three parts, folding gently with a spatula after each addition to avoid dry pockets. The dough will be thick.
Prepare the Pumpkin Pie Filling: In a medium bowl, whisk together the egg, brown sugar, salt, pumpkin spice, whole milk, pumpkin puree, and vanilla extract until smooth and blended. Set aside.
Shape and Roll Dough Balls: Using a medium cookie scoop, portion the dough into 2-tablespoon balls (about 36g each). Roll each dough ball in the coarse sugar to coat evenly. Place the sugar-coated dough balls onto the prepared cookie sheet, spacing them about 2 inches apart.
Create Wells and Fill Cookies: Using a 1-tablespoon measuring spoon or the bottom of a medicine cup, gently press down in the center of each dough ball to form a well. Fill each well with approximately 1 tablespoon of the prepared pumpkin pie filling.
Bake the Cookies: Bake in the preheated oven for 14 to 17 minutes, or until the cookies are set and the bottoms turn a light golden brown. Remove from oven, then transfer the cookies to a wire rack to cool completely.
Repeat Baking: Repeat the dough shaping, filling, and baking process with any remaining dough, ensuring the cookie sheet is cooled before adding more dough balls to maintain cookie shape and texture.
Serve: When ready to serve, optionally top each cookie with a dollop or piped swirl of whipped cream or Cool Whip. Sprinkle a little extra pumpkin pie spice or cinnamon on top for extra flavor and presentation. Enjoy warm or at room temperature.

Notes

To create the well in the dough balls, you can also use the bottom of a plastic medicine cup (such as the one that comes with Pepto Bismol) for an even, consistent indentation.
Only add whipped cream or cool whip topping to cookies just before serving to maintain freshness and texture.
Store leftover cookies in an airtight container at room temperature for up to 3 days. For longer storage, refrigerate and bring to room temperature before serving to restore optimal flavor and texture.
Cookies freeze well when sealed in an airtight container with wax paper layered between each cookie to prevent sticking.
Nutritional information is an estimate calculated using an ingredient database and does not include optional garnishes.

Prep Time: 30 minutes
Cook Time: 15 minutes
Category: Dessert
Method: Baking
Cuisine: American

Keywords: Pumpkin Pie Cookies, Fall Cookies, Pumpkin Spice Cookies, Thumbprint Cookies, Holiday Cookies, Pumpkin Dessert