Step 1

Heat oven to 400°F. Cut the squash in half with a large, sharp knife and remove seeds with a spoon. Lightly brush the cut side of a squash with canola oil. Line a rimmed baking sheet with foil and brush lightly with canola oil. Place the cut side of the squash down and bake until the skin is soft and easily pierced with a skewer, about 40 minutes. Allow to cool, then scoop the flesh from the skin with a spoon. Puree until smooth using a food processor or immersion blender. Measure out 3 cups of pureed squash. Reserve the rest for another use.

Step 2

Whisk 1 cup half and half, 1 cup milk, 3 large eggs, 2 large egg yolks, and 1 teaspoon vanilla together in a medium bowl. Set aside.

Step 3

Move oven rack to lowest position. Place a rimmed baking sheet on the rack and preheat it at 400°F. Line your pie shell with 2 layers of foil, ensuring to cover edges of crust and fill with pie weights (or dried beans - you will not be able to cook with the beans after this). Bake on the heated baking sheet for 15 minutes. Remove foil and pie weights and bake for an additional 5-10 minutes, until golden brown. Remove from oven - pie shell MUST still be warm when the filling is added.

Step 4

While the crust is baking, stir together 3 cups of the pureed squash, 3/4 cup brown sugar, 1/4 cup maple syrup, 2 teaspoons grated fresh ginger, 1 teaspoon salt, 1/2 teaspoon ground cinnamon, and 1/4 teaspoon ground nutmeg together in a large saucepan over medium heat. Bring to a simmer and stir constantly for 15-20 minutes, until thickened.

Step 5

Remove the pot from heat and whisk in the cream mixture until completely mixed. Transfer this mixture (it must still be warm) to the warm, prebaked pie crust.

Step 6

Bake on the baking sheet for 10 minutes at 400°F. Without opening oven, reduce heat to 300°F. Allow to bake until the edges of the pie are set and the center measures 175°F on an instant-read thermometer, at least 35 more minutes. After 35 minutes, check temperature every 10 minutes until done.

Step 7

When done, remove pie from the oven and cool on a wire rack to room temperature, 2-3 hours. The pie will set completely during this time. Serve with whipped cream if desired.