Make the Pie Dough:

The key to flaky, buttery pie crust is keeping the butter cold. In a stand mixer with the paddle attachment, combine the flour, sugar, and salt. Then, add the cold butter, mixing until the dough looks like coarse sand. Gradually add ice water, 1 tablespoon at a time, until the dough forms. Divide the dough into two discs, wrap them tightly in plastic wrap, and refrigerate for at least 1 hour. Cold dough ensures your pies will bake up perfectly.

Prepare the Bourbon Apple Filling:

Melt the salted butter in a pan over medium heat, allowing it to turn golden brown. Once ready, add your diced apples, bourbon, vanilla bean paste, ground cinnamon, and brown sugar. Stir everything together and cook for 5-7 minutes, or until the apples become syrupy and tender. Set the filling aside to cool.

Roast the Blackberries:

Preheat your oven to 400°F. Spread your fresh blackberries evenly on a baking sheet and roast them for about 30 minutes. Once roasted, transfer the blackberries to a pot, adding the sugar and vanilla extract. Simmer this mixture for 10 minutes, then let it cool before using it as a filling.

Assemble the Hand Pies:

Roll out your chilled pie dough to a 1/8-inch thickness on a floured surface. Using a pumpkin-shaped cookie cutter (about 4 inches in size), cut out your pumpkin bases. On half of the pumpkins, carve out Jack-O-Lantern faces—this is where the fun begins! Place 1 1/2 tablespoons of filling (either apple or blackberry) in the center of the uncut pumpkin shapes. Brush the edges with egg wash, top them with the Jack-O-Lantern faces, and seal the edges with a fork.

Bake to Perfection:

Preheat your oven to 375°F. Brush the tops of your hand pies with egg wash, sprinkle with turbinado sugar for extra crunch, and bake for 25 minutes or until golden brown and crisp. Allow them to cool slightly before serving!