In a stand mixer, combine all-purpose flour, granulated sugar, and kosher salt. Add the cold, diced unsalted butter, mixing until the mixture resembles coarse crumbs, about 1-2 minutes. Gradually add ice water, continue mixing until a dough forms. Shape into discs and refrigerate for at least 1 hour.

In a skillet over medium heat, melt salted butter until golden brown. Add diced Honey Crisp apples, bourbon, vanilla bean paste, ground cinnamon, and brown sugar. Cook while stirring until syrupy and apples are tender, about 10-12 minutes. Allow the filling to cool.

Preheat your oven to 400°F (200°C). Spread fresh blackberries on a baking sheet and roast for about 30 minutes until softened. In a saucepan, combine roasted blackberries with granulated sugar and vanilla extract. Simmer on low heat until thickened, around 5-7 minutes. Set aside to cool.

Once chilled, remove dough from the refrigerator. On a floured surface, roll out each disc to about 1/8 inch thick. Use a pumpkin-shaped cookie cutter to cut out pumpkin shapes and place half on a parchment-lined baking sheet. Chill for an additional 20 minutes.

Preheat your oven to 375°F (190°C). On half of the pumpkin shapes, carve jack-o-lantern faces. On uncut pieces, spoon amounts of filling—either bourbon apple or roasted blackberry—then place carved pieces on top. Seal edges with egg wash and press with a fork.

Brush the tops of assembled Jack-O-Lantern Hand Pies with egg wash and sprinkle raw sugar. Bake for 25 minutes, or until golden brown. Allow to cool on a wire rack.