Prepare the pie crust at least one hour in advance, or ideally the day before. Ensure the recipe is doubled. Combine all crust ingredients in one bowl if preferred, form into two discs, and chill thoroughly.

If using fresh cherries, wash, dry, remove stems, pit thoroughly, and cut the cherries in half. Whole cherries may be used if desired.

In a small bowl, whisk together the cornstarch and ¼ cup (59 g) of the red wine until completely smooth. Set aside.

In a medium saucepan, combine the cherries, the remaining ½ cup (118 g) red wine, brown sugar, vanilla extract, cinnamon, and cloves (if using). Heat over medium until the mixture reaches a gentle simmer. Stir frequently until the sugar dissolves.

Stir the cornstarch mixture once more, then slowly pour it into the simmering cherries while stirring continuously. Allow the mixture to cook for an additional 1–2 minutes, or until slightly thickened. Remove from heat and refrigerate for at least 15 minutes.

Preheat the oven to 400°F (205°C). Line two baking sheets with parchment paper or silicone baking mats.

Place one disc of chilled pie dough on a lightly floured work surface. Lightly dust the top of the dough with flour. Roll the dough evenly to approximately ⅛ inch (⅓ cm) thickness, rotating as needed to maintain an even shape.

Using a round cookie or biscuit cutter at least 3½ inches (9 cm) in diameter, cut out dough circles as closely together as possible. Transfer each circle to the prepared baking sheets. Gather the excess dough and set aside.

Repeat the rolling and cutting process with the second dough disc. Reserve these circles separately; they will serve as the top layers of the hand pies.

Combine the excess dough from both discs, form into a disc once more, roll to the same thickness, and cut additional circles. Divide these circles evenly between the bottom layers (on the baking sheets) and the reserved top layers.

Spoon approximately 1½ tablespoons of the chilled cherry filling into the center of each bottom dough circle. Begin with one test pie to ensure adequate sealing room.

Cover each bottom circle with a corresponding top circle. Press gently around the edges to seal. If the dough does not adhere well, lightly moisten the edges with water.

Crimp the edges with a fork to ensure complete sealing. Using a sharp knife, cut one or more small slits in the top of each pie to allow steam to escape.

If desired, brush each hand pie with the egg wash or with milk for a matte finish. Sprinkle coarse sugar on top if preferred.

Transfer the assembled hand pies to the freezer for 10–15 minutes. This step promotes a flakier crust and helps maintain the structure during baking.

Bake for 15–20 minutes, or until the crusts are golden brown and the filling is visibly bubbling. If the edges brown too quickly, loosely tent the baking sheets with aluminum foil.

Allow the Cherry Hand Pies to cool slightly before serving.