First, make the crust. In the bowl of a food processor, combine the flour, sugar, and salt, and pulse a few times to mix. Add the butter and pulse until the butter is cut into roughly dime-sized pieces. With the processor running, gradually add the water and process until the dough just begins to come together. Dump the dough out onto a floured board, form into a round, then wrap with plastic and chill for at least 1 hour or up to 24 hours.
Preheat the oven to 400 degrees and prep your pumpkin: Make vertical cuts around the stem and remove it as you would for a jack-o'-lantern. Carefully cut the pumpkin in half lengthwise and, using a spoon, remove the seeds and pulp. Save the seeds for the optional maple-roasted pumpkin seeds, or discard. Slice the pumpkin halves into wedges about 1½-inches thick and place them on a sheet pan. Drizzle with 2 tablespoons olive oil, 2 tablespoons of the maple syrup, and a pinch of salt and toss well. Roast for 40 to 50 minutes, turning the wedges halfway through, until very tender when pierced with a fork. Set aside until cool enough to handle.
On a floured surface, roll the dough into a circle about ¼-inch thick, turning and flouring the dough often to keep it from sticking. Carefully transfer to a 9-inch or 9.5-inch pie plate and lightly press the crust into the sides of the plate. Trim the edges, leaving about ½-inch of overhang. Fold the excess dough underneath at the edges and crimp the pie dough using your fingers or the tines of a fork. Chill for 30 minutes.
Line the crust with parchment paper and fill with pie weights or dried beans. Bake the crust for 15 minutes, then remove the beans and paper, prick the crust all over with the tines of a fork, and bake for another 5 to 10 minutes, until the crust is a pale gold color. Set aside to cool slightly and lower the oven temperature to 350 degrees.
Make the filling: scoop the cooked pumpkin flesh into a bowl, discarding the skins. Measure out 2 cups (packed) or 15 ounces pumpkin, saving any extra for another use. (Pumpkin pie oatmeal?!) Combine the pumpkin and milk in the bowl of a food processor and process until very smooth, stopping to scrape down the sides of the bowl if necessary. Transfer the puree to a large bowl. Add the cream, eggs, brown sugar, remaining 3 tablespoons maple syrup, cinnamon, ginger, nutmeg, cloves, ¼ teaspoon salt, and a pinch of black pepper. Whisk until smooth.
Pour the filling into the par-baked pie crust. (If you are using a 9-inch pie plate, you may have a small amount of filling leftover.) Bake for 55 to 65 minutes, or until the pie is completely set around the edges but still has a slight jiggle in the center. Cool completely and serve chilled or at room temperature, topped with lots of whipped cream and maple-roasted pumpkin seeds, if using. Note: To make the optional maple-roasted pumpkin seeds, wash the seeds, picking out any pieces of stringy pumpkin flesh, and set them on a paper towel to dry. Transfer the seeds to a sheet pan, toss with 2 teaspoons olive oil and 2 teaspoons maple syrup, and sprinkle with salt. Roast for 15 minutes at 350 degrees, then toss and continue to roast in 5 minute increments, tossing between, until the seeds are toasted and golden brown. Transfer to a dish to cool. Copyright 2020, Lidey Heuck, All Rights Reserved