1. In a stand mixer, combine flour, sugar, and salt. Add butter and mix until coarse crumbs form. 2. Drizzle in ice water until dough clumps together. Divide in two, wrap in plastic, and chill 1 hour. 3. For the apple filling, cook butter in a pan until browned. Add apples, bourbon, vanilla, cinnamon, and sugar. Cook 5–7 minutes until thick. Cool. 4. For the blackberry filling, roast berries at 400°F for 30 minutes. Simmer with sugar and vanilla for 10 minutes. Cool completely. 5. Roll dough to 1/8-inch thickness. Cut out pumpkin shapes with cookie cutter. Chill 10 minutes. 6. Carve jack-o-lantern faces on half the cutouts. Place non-face cutouts on a tray and spoon 1½ tbsp of filling in the center. 7. Brush edges with egg. Place face cutouts on top and seal with a fork. 8. Brush tops with egg and sprinkle turbinado sugar. Bake at 375°F for 25 minutes until golden brown. 9. Cool on wire rack and serve warm or at room temperature.