Perfect for a Halloween party or a fall family dinner, you can either use fresh pumpkin or canned puree.
For the Crust
1 cups whole-wheat pastry flour
½ cup all-purpose flour, plus more for dusting
1 tablespoon maple sugar or brown sugar
¼ teaspoon salt
4 tablespoons cold unsalted butter, cut into chunks
2 tablespoons avocado oil or organic canola oil
3 to 5 tablespoons ice water
For the Filling
4 ounces unsweetened chocolate, chopped
2 tablespoon unsalted butter
1 cup dark maple syrup
4 large eggs, divided
2 tablespoons unsweetened cocoa powder
1.75 cups pumpkin puree (from a can or fresh)
½ cup half and half
2 teaspoons pumpkin pie spice
1 teaspoon vanilla extract
Make crust: Pulse whole-wheat pastry flour, all-purpose flour, maple sugar and salt in food processor. Add butter, and process until the butter is cut in and the mixture resembles coarse meal. Open lid, drizzle on oil and pulse to combine. Open lid and drizzle on 3 tablespoons ice water. Process until the mixture just comes together. If the mixture seems dry or does not come together as a ball, try squeezing a handful of the crumbs together. If it still won’t come together, add up to 2 more tablespoons water. Form dough into a disk, wrap in plastic and refrigerate until firm and chilled, at least 1 hour.
Arrange oven rack in the lower third of the oven. Preheat oven to 375 degrees F. Roll dough out to a circle, about 14-inches across. Transfer to a 9-inch pie plate and crimp edges. Chill crust while you prepare filling.
Make Filling: Melt chocolate and butter in a small saucepan over low heat, stirring constantly. Remove from the heat and whisk in ½ cup maple syrup. Whisk in 1 egg. Whisk in cocoa powder. Set aside.
Whisk pumpkin puree, half and half, pumpkin pie spice, vanilla extract, the remaining ½ cup maple syrup and the remaining 3 eggs. Whisk 1/3 cup pumpkin mixture into the chocolate mixture to loosen it. Pour 2/3 of the remaining pumpkin mixture into the pie crust. Pour the chocolate mixture on top. Dot with the remaining pumpkin mixture. Run a knife through the layers to swirl.
Bake pie on the bottom rack until the crust just starts to brown, 22 to 25 minutes. Reduce oven temperature to 325 degrees F. Continue baking until the crust is browned and the filling no longer wiggles when the pie is jiggled, 25 to 30 minutes longer. Cool completely before slicing. Store in the refrigerator.