Position rack in bottom third of oven and preheat to 350° F. Roll out pie crust disk on lightly floured surface to 14-inch round. Transfer dough to 9-inch-diameter glass pie dish. Trim overhang to 1/2 inch; reserve dough scraps. Fold edge of crust under. Crimp edge decoratively, forming high-standing rim. Place crust in freezer for 15 minutes.
Line crust with foil. Fill with dried beans or pie weights. Bake until sides are just set, about 15 minutes. Remove foil and beans and bake until crust is pale golden, piercing with fork if crust bubbles, about 12 minutes. Transfer to rack; cool. Maintain oven temperature.
If desired, reroll reserved dough scraps to 1/8-inch thickness. Using small pumpkin-shaped cookie cutter, cut 1 1/2- to 2-inch-diameter pumpkins. Gater scraps into ball and reroll. Cut out additional pumpkins. Using small sharp knife, score each pumpkin decoratively. Arrange on small baking sheet. Brush pumpkins with milk; sprinkle with 1 tablespoon sugar. Bake until light golden brown, about 15 minutes. Transfer sheet to rack and cool.
Whisk pumpkin, sour cream, 1/2 cup whipping cream, brown sugar, eggs, cinnamon, ginger, nutmeg, cloves, salt and 1/2 cup sugar in large bowl to blend. Pour into prepared crust. Bake until filling puffs around edges and center is almost set, about 55 minutes. Transfer to rack and cool completely. (Can be prepared 1 day ahead. Cover cutouts and pie separately with plastic. Store cutouts at room temperature. Refrigerate pie.)
Beat 1 cup chilled cream and powdered sugar in medium bowl until stiff peaks form. Spoon whipped cream around edge of pie. Arrange pumpkin cutouts decoratively in cream.