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Special equipment: your favorite small holiday cookie cutter, a pastry bag fitted with a round pastry tip
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For the cupcakes: Position an oven rack in the center of the oven, and preheat to 350 degrees F. Line a 12-cup muffin tin with paper liners, and coat the liners and the top of the tin with cooking spray.
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Whisk the flour, pumpkin pie spice, baking powder and salt together in a large bowl.
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Whisk the pumpkin puree, granulated sugar, butter, eggs, milk and vanilla together in a medium bowl.
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Pour the pumpkin mixture into the flour mixture, and gently fold until just incorporated (it's OK if there are some lumps).
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Bake until the tops spring back when pressed, 24 to 28 minutes, rotating the tin halfway through.
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Let the muffins cool in the pan for a few minutes, then transfer to a rack to cool completely.
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(The cupcakes can be made up to 2 days before and refrigerated in an airtight container.)
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For the pie crust cutouts: While the muffins are cooling, cut out 12 shapes from the pie crust, and arrange them on a parchment-lined baking sheet.
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Brush each with milk, and sprinkle generously with granulated sugar.
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Bake until deep golden brown, 10 to 15 minutes, rotating the baking sheet halfway through.
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Let cool completely.
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For the filling/topping: Beat the cream cheese and confectioners' sugar together in a medium bowl until smooth.
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Add 1 cup of the cream, and beat until soft peaks form.
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Add the remaining 1 cup cream, and beat until stiff peaks form.
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Transfer the mixture to the prepared pastry bag.
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To fill and top the cupcakes: Use a teaspoon or a melon baller to take a small scoop out of the top center of each cupcake (save these cupcake pieces).
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Squeeze some of the filling/topping into each hole, and top with one of the cupcake pieces.
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Pipe a swirl of the filling/topping on top of each cupcake.
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(The cupcakes can be refrigerated for up to 2 hours at this point if you prefer them chilled.)
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Gently push a pie crust cutout into the frosting of each cupcake, and serve.
