Mix brown sugar, cornstarch and pie spice in medium sized pot. Stir well to remove all lumps.
Stir in 1/4 cup milk to completely dissolve cornstarch.
Stir well while adding remainder of milk, squash and egg yolks.
Cook mixture on medium high heat stirring continually until it thickens and begins to bubble. Do not boil hard. Lower heat and cook for one more minute. It will thicken and look unevenly lumpy, keep stirring.
Strain mixture through a fine sieve to remove any lumps and larger pieces of squash.
Add butter and cool for 10 minutes before assembling in final dish.
Or let cool and cover with plastic wrap pushed onto the surface of the pudding. Store in fridge for up to 4 or 5 days. The wrap prevents a crust from forming.
Makes 3 cups.
To assemble
Use a large knife to carefully cut gingersnap cookies in half. Some will crumble completely - hence the extras!
Crumble half a cookie in the bottom of each individual dish.
Layer with 1/3 cup of pudding (for 9 individual servings)
Add about 11/2 tablespoon of whipped cream to each.
Sprinkle with a light dusting of pie spice.
Garnish with remaining half of gingersnap cookie.
For one giant dessert, crumble gingersnaps in bottom of a 9x9 inch pan, top with pudding and garnish with remaining cookies, whipped cream and pie spice.
Notes
The higher the per cent fat in your milk, the creamier and richer this pudding will taste. I used 1% milk because it's what we have on hand and it was delicious. To substitute for pie spice use 1 tsp cinnamon, 1/4 tsp ginger powder, 1/8 tsp nutmeg and a hint of powdered cloves. You can use puree from a variety of winter squash like pumpkin, kabocha, butternut, buttercup or hubbard. If your puree is very liquidy, drain it before using