Combine flour and 1/2 teaspoon salt; cut in shortening with a pastry blender until mixture resembles the size of peas. Sprinkle ice water, 1 tablespoon at a time, evenly over surface; stir with a fork until dry ingredients are moistened. Shape dough into a ball; cover and chill 30 minutes.
Roll dough to 1/8" thickness on a lightly floured surface. Fit into a 9" deep-dish pieplate; trim off excess pastry along edges. Fold edges under, and crimp. Line pastry with aluminum foil, and fill with pie weights or dried beans. Bake at 450° for 8 minutes. Remove weights and foil; bake pastry 4 more minutes. Remove pastry crust to a wire rack to cool; reduce oven temperature to 375°.
Whisk together butternut squash and next 10 ingredients in a large bowl until combined. Pour filling into crust.
Bake at 375° for 50 to 55 minutes or until a knife inserted near center comes out clean, shielding crust after 20 minutes. Cool on a wire rack. Cover and refrigerate overnight.
Combine 2 tablespoons granulated sugar and pecans in a small skillet. Cook over medium-low heat, stirring constantly, 5 minutes or until sugar melts and pecans are toasted. Spoon onto wax paper to cool. Crumble sugared pecans into pieces.
Beat whipping cream at high speed with an electric mixer until foamy; gradually add powdered sugar, 1 tablespoon at a time, until soft peaks form. Slowly fold maple syrup into whipped cream. Cover and chill 1 hour.
To serve, spoon maple cream onto each serving. Sprinkle sugared pecans over cream.