Roast butternut squash: Cut your butternut squash into quarters, removing the seeds and discarding or saving to use in another recipe of to roast for a snack. Drizzle oil on your butternut squash, and bake cut side up at 375 degrees for 35-40 minutes or more until it is done. You want the butternut squash to be very soft and easily poked with a knife.
When your butternut squash is ready, let cool and peel, removing the skin of your swum and leaving the flesh.
Place your butternut squash in a blender or food processor and pulse until very smooth.
Measure out 3 cups of butternut squash and set aside. If you have leftovers, you can use this to make a number of other dishes.
In a pan, add your butternut squash and brown sugar, cook on low heat, stirring consistently until the water from the squash evaporates, is reduced significantly in volume and get thick and dark. You want to cook it down as much as possible into a thick paste. This usually takes me about 30 minutes.
Set aside and let cool completely before continuing.
Preheat oven to 350 degrees.
In a bowl mix together your butternut squash and sugar paste, egg yolk, eggs, condensed milk, cream, vanilla, salt and ground spices. Whisk until very smooth and pour in prepared pie crust. Add 3/4 cup of cream first and if filling is too thick, add another 1/4 cup of whipped cream. The amount of cream varies based on how much you cooked down your butternut squash. Filling is too thick if it can't be easily poured or if it holds its shape (i.e. it is too thick it the pie filling needs to be smoothened flat, as opposed to just setting into a flat surface).
Bake for 50-60 minutes in preheated oven, or until the custard is just set. The edges of the custard will puff up a little and the centre should still have a little wiggle to it.
Let cool for at least 2 hours and serve at room temp or chilled. Pie tastes just as good the next day. Store in an airtight container in refrigerator. Serve with whipped cream of ice cream.