Freeze your ice cream maker 24-48 hours ahead of time.
Preheat oven to 325 degrees.
Gut acorn squash and cut into fours.
(You'll only need half of the squash for this recipe, but you can cook it all if you like. Just double the spice.)
Mix whiskey and spices together, brush over squash, and place in a baking pan covered with foil. Bake for 30-45 minutes until completely tender. Letting the squash steam in the bourbon.
While the squash cooks, heat milk, cream, sugar, and vanilla extract together in a stove pot. Whisk until the sugar is dissolved. Don’t let it boil.
Once the liquid is warm, use a mixing bowl to slowly whisk the warm cream into the egg yolks. Tempering the yolks so as not to curdle them.
Remove from heat and chill it in the refrigerator.
When the squash has cooked, let it cool to a manageable temperature, then scoop out the flesh with a spoon. Purée the squash in a bowl with an immersion blender.
Slowly add cream until it is one smooth consistency.
Strain through a wire mesh to make sure no bits of squash are left.
Follow instructions on your ice cream maker.
Serve with an extra garnish of pumpkin pie spice.
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