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1
If decorating your pie with sugared cranberries, start them the night before. You'll also begin the pie crust the night before as well (the dough needs at least 2 hours to chill; overnight is best). The filling can be made the night before as well. In fact, I prefer it that way. It gives the spices, pumpkin, and brown sugar flavors a chance to infuse and blend. It's awesome. Cover and refrigerate overnight.
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2
For the cranberries: Place cranberries in a large bowl; set aside. In a medium saucepan, bring 1 cup of sugar and the water to a boil and whisk until the sugar is dissolved. Remove pan from the heat and allow to cool for 5 minutes. Pour sugar syrup over the cranberries and stir. Let the cranberries sit at room temperature or in the refrigerator for 6 hours or overnight (ideal). You'll notice the sugar syrup is quite thick after this amount of time. Drain the cranberries from the syrup and pour 1 cup of sugar on top. Toss the cranberries, coating them all the way around. Pour the sugared cranberries on a parchment paper or silicone baking mat-lined baking sheet and let them dry for at least 2 hours.
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3
Make the pie crust through step 5 according to my directions and visuals.
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4
For the FILLING: Whisk the pumpkin, 3 eggs, and brown sugar together until combined. Add the cornstarch, salt, cinnamon, ginger, nutmeg, cloves, pepper, cream, and milk. Vigorously whisk until everything is combined. Filling will be a little thick.
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5
Preheat oven to 350F (180C) degrees.
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6
Make the pie crust leaves: On a floured work surface, roll out one of the balls of chilled dough (keep the other one in the refrigerator). Roll out into any shape you really want (doesn't matter) and 1/8 inch thickness. Using leaf cookie cutters, cut into shapes. Brush each lightly with the beaten egg + milk mixture. Cut leaf veins into leaves using a sharp knife, if desired. Place onto a parchment paper or silicone baking mat-lined baking sheet and bake for 10 minutes or until lightly browned. Remove and set aside to cool.
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7
Turn oven up to 375F degrees. The pie will bake at 375F.
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8
Roll out the chilled pie crust: Remove second pie dough from the refrigerator. On the same floured work surface, turn the dough about a quarter turn after every few rolls until you have a circle 12 inches in diameter. Carefully place the dough into a 9-inch deep dish pie (one that is 1.5 - 2 inches deep). Tuck it in with your fingers, making sure it is smooth. With a small and sharp knife, trim the extra overhang of crust and discard. Crimp the edges with your fingers, if desired. Brush edges lightly with beaten egg/milk mixture. Using pie weights, pre-bake the crust for 10 minutes.
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9
Pour pumpkin pie filling into the warm pre-baked crust. If you did not use a deep dish pie pan, you will have too much filling. Only fill the crust about 3/4 of the way up. Use extra to make mini pies with leftover pie dough scraps if you'd like. Bake the pie until the center is almost set, about 55-60 minutes give or take. A small part of the center will be wobbly - that's ok. After 25 minutes of baking, be sure to cover the edges of the crust with aluminum foil or use a piecrust shield to prevent the edges from getting too brown. Check for doneness at minute 50, and then 55, and then 60, etc.
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10
Once done, transfer the pie to a wire rack and allow to cool completely for at least 3 hours. Decorate with sugared cranberries and pie crust leaves. You'll definitely have leftover cranberries - they're tasty for snacking. Serve pie with whipped cream if desired. Cover leftovers tightly and store in the refrigerator for up to 3 days.
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11
Make ahead tip: Pumpkin pie freezes well, up to 3 months. Thaw overnight in the refrigerator. As mentioned in step 1, the filling can be made the night before. Pie crust dough freezes well for up to 3 months. Thaw overnight in the refrigerator before using.
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12
*3/4 teaspoon pumpkin pie spice can be used instead of these spices.
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13
**Fresh cranberries, not frozen. The sugar syrup doesn't coat evenly on the frozen berries, leaving you with rather ugly and some very plain shriveled cranberries.
