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Bake-Ahead Thanksgiving Cookies Recipe: Pumpkin Pie on a Cookie

Wide brown sugar cookies with spiced pumpkin pie filling baked into the top, finished at the table with whipped cream and a dusting of pumpkin pie spice. They bake up to 3 days ahead and wait in the fridge, so the oven stays free for the turkey.
Prep Time20 minutes
Bake Time12 minutes
Course: Dessert, Snack
Cuisine: American
Keyword: Bake Ahead, Fall, Filled Cookies, Pumpkin, Thanksgiving, Whipped Cream
Servings: 15 - 18 cookies
Calories: 250kcal
Author: Chop and Cheers

Ingredients

Cookies

  • ½ cup unsalted butter 113 g, melted
  • 1 cup brown sugar 213 g, packed
  • ½ cup granulated sugar 100 g
  • 2 large eggs
  • 1½ teaspoons vanilla extract 7.5 ml
  • 3 cups all-purpose flour 360 g
  • 1½ teaspoons baking soda 9 g
  • ½ teaspoon baking powder 2 g
  • ¼ teaspoon teaspoon salt 1.5 g
  • 2 teaspoons pumpkin pie spice 5 g

Pumpkin pie filling

  • ⅔ cup pumpkin puree 163 g, plain, not canned pumpkin pie filling
  • 1 large egg
  • ¼ cup brown sugar 53 g, packed
  • 2 tablespoons milk 30 ml
  • 1 teaspoon vanilla extract 5 ml
  • 2 teaspoons cornstarch 5 g
  • ½ teaspoon 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. Whisk it in a large bowl with both sugars, then 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, keeping it in the fridge between trays and freezing each tray for 10 minutes before filling.
  • Refrigerate the cooled cookies in an airtight container for up to 3 days.
  • Just before serving, top each cold cookie with whipped cream and a dusting of pumpkin pie spice.

Notes

  • Bake ahead: keep the bare cookies in the fridge in a single layer or with parchment between layers for up to 3 days, or freeze them for up to 2 months and thaw in the fridge overnight. Don't leave them out for more than 2 hours. The filling can be whisked a day before baking.
  • Trays: two trays can bake at once if they fit, swapped halfway through. Each tray needs its 10 minutes in the freezer before filling.
  • Topping: add the whipped cream only once the cookies are cold, right before serving.