Pumpkin Pie Cookies

close up of plate of circle cookies with pumpkin filling, crumbles, and whipped cream topping

These Pumpkin Pie Cookies feature a soft and chewy sugar cookie base, pumpkin pie filling, buttery streusel crumble, and a sweet sugary glaze. Topped with cinnamon sugar and a dollop of whipped cream, you get all your favorite parts of pumpkin pie in these adorable hand-held treats! Perfect for the holiday season and cookie exchanges!

Course Dessert

Cuisine American

Prep Time 15

Cook Time 10

Chill Time 30

Total Time 55

Servings cookies

Calories 265kcal

Author Tawnie Graham of Kroll's Korner

Ingredients

For the Cookie Base:

1 cup unsalted butter, cold, cut into cubes If using salted butter, don't add extra salt
1 cup powdered sugar
1 large egg
1 large egg yolk
2 tsp. vanilla extract
¼ tsp. almond extract optional
2¾ cups all-purpose flour spooned and leveled
2 tsp. baking powder
½ tsp. salt omit if using salted butter
2-4 tsp. milk if needed

For the Pumpkin Filling:

¾ cup 100% pumpkin puree, blotted Measure ¾ cup AFTER moisture is blotted out, which is basically 1, 15 oz. can. I used paper towels to blot.
½ cup granulated sugar
Pinch pumpkin pie spice Not too much because it makes the pumpkin look dark and weird.
1 tsp. cornstarch
Pinch kosher salt
1 tsp. vanilla

For the Crumble Topping:

1 cup flour
1 1/4 tsp. baking powder
1/2 cup granulated sugar
1 tsp. vanilla extract
6 Tbsp. butter, melted
¾ tsp. salt

For the Powdered Sugar Glaze:

2 cups powdered sugar
2-4 tbsp. whole milk (or half & half)
1 tsp. vanilla extract (or clear vanilla extract)

Optional for Garnish:

1 tsp. cinnamon
3 tbsp. granulated sugar
whipped cream

US Customary - Metric

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Instructions

Prepare the Cookie Dough:

Using a stand mixer with a paddle attachment (or a hand mixer), add the powdered sugar and salt to the bowl and mix to combine.
1 cup powdered sugar, ½ tsp. salt
Add the cold butter pieces and beat on low to start, then increase the speed. Beat until the butter and sugar form almost like a paste. Scrape down the sides of the bowl as needed.
1 cup unsalted butter, cold, cut into cubes
Add in the egg, egg yolk, vanilla extract and almond extract (if using).
1 large egg, 1 large egg yolk, 2 tsp. vanilla extract, ¼ tsp. almond extract
Add the flour and baking powder and mix just until combined. If the dough seems dry, add a splash of milk.
2¾ cups all-purpose flour, 2 tsp. baking powder, 2-4 tsp. milk
Divide the dough in half.
Place each half of dough on a sheet of parchment paper. Place a second sheet of parchment paper on top of each half of dough.
Using a rolling pin, roll out each half of dough between the 2 sheets of parchment until ~⅜ inch thick. (Tip: ⅜ inch thick is right in between ¼ and ½ inch thick.) I like them a little thick, so they have a nice chew!
Then, freeze the dough until cold (20-30 minutes or longer if needed).

Prepare the Pumpkin Filling:

Meanwhile, mix together the pumpkin filling ingredients until smooth. (Or you can use a hand mixer if you prefer.)
¾ cup 100% pumpkin puree, blotted, ½ cup granulated sugar, Pinch pumpkin pie spice, 1 tsp. cornstarch, Pinch kosher salt, 1 tsp. vanilla

Prepare the Crumble Topping:

In a bowl, stir together all the crumble topping ingredients until the dough comes together. You should be able to pinch it between your fingertips and it stays together. If not, add a little more melted butter.
1 cup flour, 1 1/4 tsp. baking powder, 1/2 cup granulated sugar, 1 tsp. vanilla extract, 6 Tbsp. butter, melted, ¾ tsp. salt

Bake the Cookies:

Preheat the oven to 350°F. Line a couple baking sheets with parchment paper.
Using a 2 ½ inch circular cookie cutter, cut the cookies into circles.
Spread some of the pumpkin filling on each cookie, spreading it all the way to the edges of the cookie.
Top with a generous amount of the streusel crumble topping. Don’t be shy!
Bake for ~9-11 minutes or until you can start to see the edges begin to brown and the crumble looks a little golden. Careful not to over-bake.
Remove from oven and allow to cool on cookie sheet for a couple minutes then carefully transfer to a wire rack.

Finish with Toppings:

Mix together the cinnamon and sugar until combined.
1 tsp. cinnamon, 3 tbsp. granulated sugar
Whisk together the ingredients for the glaze.
2 cups powdered sugar, 2-4 tbsp. whole milk (or half & half), 1 tsp. vanilla extract (or clear vanilla extract)
Sprinkle a little of the cinnamon-sugar topping on top of the streusel, and then drizzle the glaze over the cooled cookies.
(Optional) You can add a little dollop of piped whipped cream on top of the cookies too, if you're extra, like me!
whipped cream

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Notes

I recommend keeping these at room temperature in an airtight container for up to 3 days (without the whipped cream garnish), refrigerating for up to 1 week, or freezing for up to 2 months.

You can freeze the sugar cookie dough for up to 3 months.

Nutrition