In a large bowl, whisk together flour, salt, and sugar. Add the cold cubed butter and use a pastry cutter or your fingertips to work it into the flour until the mixture resembles coarse crumbs with some pea-sized pieces remaining.
Gradually add ice water, 1 tablespoon at a time, stirring with a fork until the dough just begins to come together. Divide the dough into two portions – one slightly larger (about 60%) for the bottom crust and a smaller portion (about 40%) for the Jack-o'-Lantern face.
Form each portion into a disk, wrap in plastic, and refrigerate for at least 30 minutes.
Preheat your oven to 375°F (190°C). On a lightly floured surface, roll out the larger disk to a 12-inch circle, about ⅛-inch thick. Carefully transfer to a 9-inch pie dish, gently pressing into the bottom and sides.
Trim the excess, leaving a ½-inch overhang, then fold under and crimp decoratively. Prick the bottom several times with a fork.
Line the crust with parchment paper and fill with pie weights or dried beans. Blind bake for 15 minutes, then remove the weights and parchment and bake for an additional 5 minutes until the crust is just beginning to color.
While the crust is baking, whisk together the pumpkin puree, brown sugar, maple syrup, pumpkin pie spice, and salt until well combined.
In a separate bowl, lightly beat the eggs, then stir them into the pumpkin mixture along with the heavy cream and vanilla extract.
Roll out the remaining dough to about ⅛-inch thickness. Using paring knives or small cookie cutters, cut out Jack-o'-Lantern facial features – triangular eyes, a nose, and a grinning or spooky mouth.
Place your cut pieces on a parchment-lined baking sheet and refrigerate them while you pour the filling.
Pour the maple pumpkin filling into the par-baked crust. Carefully arrange your pre-cut Jack-o'-Lantern features on top of the filling to create a face. For an extra touch, add a small stem-shaped piece at the top of the pie.
Brush the dough features with egg wash for a golden shine. Cover the crimped edges with a pie shield or aluminum foil to prevent over-browning.
Bake for 50-55 minutes, or until the filling is just set but still slightly jiggly in the center (it will continue to set as it cools).
Allow the pie to cool completely for at least 2 hours before slicing and serving.