Description

These thick and chewy Pumpkin Pie Cookies feature a crisp bottom with a smooth, silky pumpkin pie filling in the center. They combine the warm, aromatic flavors of pumpkin spice in both the cookie dough and filling, making them perfect for fall and holiday gatherings. These cookies are a delightful cross between classic pumpkin pie and spiced cookies, ideal for pumpkin lovers looking for a handheld treat.

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 brown sugar, packed (112g)
1 large egg yolk, room temperature
1 teaspoon vanilla extract
⅓ cup coarse sugar for rolling (78g)

For the Pumpkin 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

Optional Topping:

Whipped cream or Cool Whip for serving

Instructions

Preheat the Oven: Preheat your oven to 350℉ (175℃). Line a cookie sheet with parchment paper and set it aside to prepare for baking the cookies.
Prepare the Cookie Dough: In a medium bowl, whisk together the all-purpose flour, pumpkin spice, and salt. In a large mixing bowl, combine the room temperature cream cheese, unsalted butter, granulated sugar, and brown sugar. Beat on medium-high speed with an electric mixer until the mixture is fluffy, about 3 minutes. Scrape down the sides and bottom of the bowl, then blend again. Add the egg yolk and vanilla extract, blending until fully incorporated. Gradually add the flour mixture in three parts, folding gently with a spatula to ensure there are no dry spots, resulting in a thick dough.
Prepare the Pumpkin Filling: In a medium bowl, whisk together the pumpkin pie filling ingredients: egg, brown sugar, salt, pumpkin spice, whole milk, pumpkin puree, and vanilla extract. Mix until smooth and well combined. Set aside.
Form and Coil the Cookies: Using a medium cookie scoop, portion the dough into 2-tablespoon balls (approximately 36 grams each). Roll each dough ball in the coarse sugar to coat thoroughly. Place the coated dough balls on the prepared cookie sheet about 2 inches apart to allow room for baking.
Create Wells and Fill Cookies: With a 1-tablespoon measuring spoon or the bottom of a medicine cup, gently press down on each dough ball to create a well in the center without breaking through the bottom. Carefully fill each well with 1 tablespoon of the prepared pumpkin filling, distributing evenly.
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. Avoid overbaking to maintain the chewy texture. Remove the cookies from the oven and transfer them to a wire rack to cool completely.
Repeat Baking Batches: If baking in multiple batches, allow the cookie sheet to cool between batches to prevent dough spreading and improve cookie texture.
Serve and Garnish: Serve the cookies slightly warm or at room temperature. Optionally, pipe or dollop whipped cream or Cool Whip on top of each cookie and sprinkle with additional pumpkin pie spice or cinnamon for an enhanced presentation and flavor.

Notes

To create the wells in the dough balls, you can use the bottom of a plastic medicine cup like the one included with Pepto Bismol for a uniform shape.
Only add whipped cream or Cool Whip to the cookies immediately before serving to maintain freshness and texture.
Store leftover cookies in an airtight container at room temperature for up to three days or refrigerate for longer storage. Bring refrigerated cookies to room temperature before serving for the best flavor.
Cookies freeze well when sealed in an airtight container with wax paper between layers; thaw before serving.
For dairy-free substitutions, consider using vegan butter and vegan cream cheese, and substitute whole milk with a non-dairy milk alternative.

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

Keywords: pumpkin pie cookies, pumpkin cookies, thumbprint cookies, pumpkin spice cookies, fall desserts, holiday cookies, pumpkin pie filling, chewy pumpkin cookies, spiced cookies, pumpkin dessert