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To make the filling: In a medium bowl, whisk together all the filling ingredients.
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Preheat oven to 350°F with a rack in the lower third and lightly grease two mini muffin pans. (If you only have one pan, see “tips,” below.)
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To assemble: Remove one piece of pie pastry from the refrigerator. Working on a lightly floured surface, roll out the dough to a 15" or 16" square, a scant 1/8" thick.
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Use a 3" round cutter to cut rounds from the dough as close together as possible. Set the scraps aside.
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Repeat the rolling and cutting process (steps 3 and 4) with the second piece of pastry.
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Gather all the scraps from both pieces of dough, gently fold the dough over on itself several times to help it come together, then re-roll until it’s about 1/8" thick. Cut additional rounds for a total of about 48. (You’ll have some remaining scrap that can be discarded or baked off as a baker’s treat!)
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Fit the dough rounds into the cups of the prepared muffin pan, pressing the dough into the bottom and up the sides of each well. (The edges will fold a bit and create a rustic look; that’s OK.)
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Transfer the filling to a large liquid measuring cup (if you use a 2-cup measure, you’ll need to refill it once partway through). Gently pour about 1 tablespoon of filling into each mini crust, filling all the way to the top.
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Bake one pan of mini pies on the lower rack of the oven for 30 to 35 minutes or until the exposed edges are golden brown and the custard is set in the center; place the second pan in the refrigerator to chill while the first batch bakes. Toward the end of the baking time, lift up one of the baked Mini Pumpkin Pies with a small offset spatula to check the bottom crust and better evaluate the color.
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Remove the mini pies from the oven and place on a wire rack to cool completely before removing from the pan, meanwhile, repeat the baking process with the second pan of mini pies.
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To make the whipped cream: Just before serving, whip the heavy cream, confectioners’ sugar, and vanilla in the bowl of a stand mixer fitted with the whisk attachment on medium-high until stiff peaks form. Transfer the whipped cream to a piping bag and pipe a rosette on each mini pie, if desired. Mini Pumpkin Pies can be served at room temperature or cold from the refrigerator.
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Storage instructions: Leftover Mini Pumpkin Pies can be stored in an airtight container in the refrigerator for up to 3 days or frozen, without whipped cream topping, for up to 3 months. Allow frozen mini pies to thaw in the refrigerator before enjoying.
