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Pumpkin Pie Cookies with Custard Filling and Whipped Cream

A spiced brown sugar cookie with a pumpkin pie custard baked into the top, finished with whipped cream and a dusting of pumpkin pie spice. There's no pie crust to roll out, the dough needs only a whisk and a spatula, and the filling can be mixed a day ahead.
Prep Time20 minutes
Bake Time12 minutes
Course: Dessert
Cuisine: American
Keyword: Fall, Filled Cookies, Pumpkin, Thanksgiving, Whipped Cream
Servings: 15 - 18 cookies
Calories: 250kcal
Author: Chop and Cheers

Ingredients

Cookies

  • 1/2 cup unsalted butter, melted 113 g
  • 1 cup brown sugar 213 g, packed
  • 1/2 cup granulated sugar 100 g
  • 2 large eggs
  • 1 1/2 tsp vanilla extract 7.5 ml
  • 3 cups all-purpose flour 360 g
  • 1 1/2 tsp teaspoons baking soda 9 g
  • 1/2 tsp teaspoon baking powder 2 g
  • 1/4 tsp teaspoon salt 1.5 g
  • 2 tsp pumpkin pie spice 5 g

Pumpkin pie filling

  • 2/3 cup pumpkin puree, plain, NOT pumpkin pie filling 163 g
  • 1 large egg
  • 1/4 cup brown sugar 53 g, packed
  • 2 tbsp milk 30 ml
  • 1 tsp vanilla extract 5 ml
  • 2 tsp cornstarch 5 g
  • 1/2 tsp pumpkin pie spice 1 g

Topping

  • Whipped cream homemade or ready-made
  • pumpkin pie spice for dusting

Instructions

  • Heat the oven to 350°F (175°C) and line a rimmed baking sheet with parchment.
  • Melt the butter and let it cool for a few minutes. Pour it into a large bowl and whisk in both sugars.
  • Whisk in the eggs and vanilla until smooth.
  • Stir the baking soda, baking powder, salt and pumpkin pie spice into the flour. Add to the bowl and fold with a spatula until no dry flour remains.
  • Scoop with a 2 inch (5 cm) cookie scoop onto the sheet, 2 inches (5 cm) apart, about 8 per sheet.
  • Press a deep well into each ball without pressing through the bottom. Pinch closed any cracks in the walls.
  • Freeze the tray for 10 minutes.
  • Meanwhile, whisk the pumpkin puree, egg, brown sugar, milk and vanilla until smooth, then whisk in the cornstarch and pumpkin pie spice.
  • Fill each well to just below the rim, about 2 teaspoons each.
  • Bake 12 minutes, until the cookies have spread, the edges are golden brown and the filling looks set.
  • Cool on the sheet for 5 minutes, then on a wire rack until completely cool.
  • Repeat with the remaining dough, freezing each tray for 10 minutes before filling.
  • Just before serving, top each cookie with whipped cream and a dusting of pumpkin pie spice.

Notes

  • Storage: refrigerate once cool in an airtight container, in a single layer or with parchment between layers, for up to 3 days. Don't leave them out for more than 2 hours. Add the whipped cream just before serving.
  • Make ahead: the filling keeps covered in the fridge for 1 day. Bare baked cookies freeze for up to 2 months; thaw in the fridge overnight.
  • Timing: the total covers the first tray, including 10 minutes in the freezer and cooling.