Not exactly the Pilgrim's version, but a delicious historical twist on an American favorite!
Preheat the oven to 350 degrees.
Cut the tops off the squash and scoop out the seeds. Place the tops back on the squash. Place on a baking sheet and bake for about 50 minutes or until the squash are fork tender.
Carefully scoop out the flesh, leaving about 1/4 inch thickness of flesh intact around the sides and bottom. Scoop out the flesh in the tops as well. You should have about 1 1/2 cups flesh from the three squash combined. (Make sure you don't puncture the skins or your pie filling will all run out!)
Place the scooped out squash, along with the sugar, maple syrup, molasses, spices, eggs, and cream in a blender. Blend until very smooth. Place the squash shells on the baking sheet. Pour the filling into the shells so that it’s evenly distributed amongst the three shells (you should have enough filling to completely fill all three shells).
Bake with the tops off (place the tops on the baking sheet as well) for 45-50 minutes until the filling is set. Remove from the oven and let cool.
Top with crumbled gingersnaps and whipped cream.