Pumpkin Pie Cookies

By Ben · cooked up in Sprig

Buttery snickerdoodle-spiced rings stacked two layers high cradle a spiced pumpkin custard filling that smells exactly like a November kitchen — warm cinnamon, clove, and brown sugar hitting the oven all at once. The crust has a satisfying snap at the edge and a tender crumb underneath the filling, where the pumpkin sets into something silky and just barely firm. A dollop of whipped cream on top makes each one look like a tiny pie pulled straight from a holiday spread. These are the kind of thing you bring to a gathering and watch disappear before the main course is even served.

Ingredients

• 2 1/4 cups all-purpose flour
• 3/4 cup granulated sugar
• 1 teaspoon ground cinnamon
• 1/2 teaspoon fine salt
• 1/2 teaspoon cream of tartar
• 1/4 teaspoon baking soda
• 1 cup unsalted butter, cold and cut into small cubes
• 1 egg yolk
• 1 teaspoon pure vanilla extract

• 3/4 cup canned pumpkin puree
• 1/4 cup heavy cream
• 1/4 cup packed light brown sugar
• 1 large egg
• 1 teaspoon ground cinnamon
• 1/4 teaspoon ground ginger
• 1/8 teaspoon ground cloves
• 1/8 teaspoon ground nutmeg
• 1/8 teaspoon fine salt
• 1 teaspoon pure vanilla extract

• 1 cup heavy whipping cream
• 2 tablespoons powdered sugar
• 1/2 teaspoon pure vanilla extract
• Ground cinnamon, for dusting

Instructions

1. In a large bowl, whisk together the flour, granulated sugar, cinnamon, salt, cream of tartar, and baking soda. Add the cold cubed butter and use your fingertips or a pastry cutter to work it into the flour until the mixture resembles coarse, pea-sized crumbles. Do not overwork — you want visible butter pieces for flakiness.
2. In a small bowl, whisk together the egg yolk and vanilla extract. Drizzle over the flour-butter mixture and stir with a fork until the dough just comes together. Turn it out onto a lightly floured surface, press into a flat disk, wrap in plastic wrap, and refrigerate for at least 30 minutes.
3. Preheat your oven to 350°F. Line two baking sheets with parchment paper. On a lightly floured surface, roll the chilled dough out to a thickness of about 1/4 inch.
4. Using a 2 1/2-inch round cookie cutter, cut out 24 rounds. Then use a 1 1/4-inch round cutter to cut the center out of 12 of those rounds, creating 12 rings (the crust walls) and leaving 12 solid rounds (the crust bases). Re-roll scraps as needed.
5. Place one solid round base on the parchment-lined baking sheet. Brush the top edge of the base lightly with water, then press a ring on top, aligning the edges carefully to create a shallow well. Repeat with remaining bases and rings. You should have 12 assembled cookie cups. Transfer the baking sheets to the freezer for 10 minutes to firm up.

1. While the cookie cups chill, make the filling. In a medium bowl, whisk together the pumpkin puree, heavy cream, brown sugar, egg, cinnamon, ginger, cloves, nutmeg, salt, and vanilla until completely smooth.
2. Remove the chilled cookie cups from the freezer. Using a small spoon or a piping bag, carefully fill each cookie well with pumpkin filling, stopping just below the top edge of the ring — about 1 1/2 to 2 teaspoons of filling per cookie. Do not overfill or the custard will bubble over.
3. Bake at 350°F for 18 to 22 minutes, until the shortbread crust is lightly golden at the edges and the pumpkin filling is just set — it should have a very slight jiggle in the center like a classic pumpkin pie. Remove from oven and allow to cool on the baking sheet for 10 minutes, then transfer to a wire rack to cool completely. The filling will firm up as it cools.

1. Make the whipped cream: In a chilled bowl, beat the cold heavy whipping cream, powdered sugar, and vanilla with a hand mixer or stand mixer on medium-high until soft to medium peaks form.
2. Transfer the whipped cream to a piping bag fitted with a star tip. Pipe a small rosette onto the center of each cooled pumpkin cookie. Lightly dust the tops with ground cinnamon and serve immediately, or refrigerate for up to 24 hours until ready to serve.

Chef's tips

Nutrition (per serving, estimated)

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