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1
For the squash: Preheat the oven to 375 degrees F.
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2
Put the squash on a sheet tray, toss lightly with olive oil and toss in the oven.
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3
Roast the squash until a fork slides in and out easily, about 45 minutes.
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4
Remove the squash from the oven and let cool.
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5
Remove the skin and puree until smooth.
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6
Place 3 cups squash puree in a large mixing bowl, reserve the rest for another purpose.
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7
For the crust: In the bowl of a food processor combine all the flour, sugar, cinnamon, allspice, ginger, nutmeg and salt.
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8
Toss in the butter and pulse until the mixture looks like grated parmigiano.
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9
Add in the egg yolk and a few drops of the ice water.
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10
Pulse until the mixture starts to come together into a ball.
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11
Add a few more drops of water if the mixture still seems dry.
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12
Turn the dough out onto a lightly floured work board.
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13
Using the heels of your hand, schmear the dough straight forward and roll it back with your fingertips.
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14
Repeat this process two more times.
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15
Form the dough into a disk, wrap in plastic and refrigerate for at least 1 hour.
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16
Remove the dough from the fridge and let warm up for 5 minutes.
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17
Roll the dough out into a large circle and lay in a deep pie dish.
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18
Trim the dough all the way around so there is only 1/2-inch overhang.
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19
Fold the dough under and crimp the edges decoratively.
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20
Make sure the edges don't extend beyond the pie plate rim.
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21
Prick the dough all over with a fork.
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22
Lay aluminum foil over the dough to cover and fill the pie plate with baking beans.
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23
Place the pie plate on a sheet tray and bake in the oven for 15 minutes.
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24
Remove the foil and baking beans and bake for 5 more minutes.
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25
Remove from the oven and let cool.
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26
Reduce the heat in the oven to 350 degrees F.
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27
For the filling: In a small bowl, beat the eggs until they are smooth.
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28
Beat in the cream.
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29
Add the cream/egg mixture to the squash puree and beat to combine.
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30
Beat in the condensed milk, brown sugar, bourbon if using and vanilla.
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31
Beat until the mixture is well combined, 1 to 2 minutes.
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32
Pour the squash mixture into the prepared pie shell.
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33
Place on the sheet tray and place back into the oven for 25 minutes.
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34
Rotate the pie and bake until the mixture barely jiggles when shaken, another 20 to 25 minutes.
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35
If the crust starts to get too dark, place a pie shield ring on the pie to protect the edges from burning.
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36
Remove the pie from the oven and let it cool for at least 1 hour before cutting.
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37
Whip heavy cream with a pinch of cinnamon until stiff peaks, and top the pie as a garnish.
