To make the apple filling: Heat butter in a stainless steel saute pan until just barely golden brown. Add the apples and cook for 2 minutes. Then, add the bourbon and cook for another minute. Add the vanilla, cinnamon, and sugar and toss to combine. Cook for 5-7 minutes until the liquid is reduced to a syrupy consistency. Cool to room temperature.

To make blackberry filling: Line a rimmed baking sheet with parchment paper and pre-heat the oven to 400 degrees F. Place the blackberries on the baking sheet and roast for 30 minutes. Transfer blackberries to a stainless steel pot with sugar and vanilla. Simmer over medium heat for 10 minutes, until thick. Cool to room temperature.

Prep the pie dough: Remove the pie dough from the refrigerator. Lightly dust a work surface with flour. Roll the dough out to 1/8th inch thick. Using a 4" pumpkin cookie cutter, cut as many pieces out as possible. Place the pumpkin pieces on a parchment-lined baking sheet and refrigerate for 20 minutes. Using a sharp knife, cut out jack-o-lantern faces on half of the pumpkin cutouts.

To assemble: Preheat an oven to 375 degrees F. Line a baking sheet with parchment paper. Lightly beat an egg in a small bowl. Place the pumpkin cutouts with no faces on the tray. Place 1 1/2 tablespoons of either filling in the center. Brush the edges around the filling with the egg. Place a pumpkin cut out with a face on top and line up the edges. Using a fork, press the edges together, sealing in the filling. Brush the top of the hand pie with egg and sprinkle with turbinado sugar, if desired. Repeat with remaining hand pies. Bake for 25 minutes, until dark golden brown. Cool on a baking rack.