Add the flour, sugars, salt and cinnamon to the bowl of a food processor. Pulse a few times to combine.
Then add the cold, cubed butter and process until the butter is pea-sized and the mixture resemble a course meal. Add the milk and pulse until the dough just starts to come together. It's ok if it's a tad shaggy.
Pour the dough out onto a clean counter and form into a round. Then divide the round in half and form each into a disc. Wrap each disc tightly with plastic wrap and place into the fridge for at least 30 minutes. Then start the filling.
In a saucepan combine the cranberries, sugar, cinnamon, water and orange juice over medium-low heat. Bring to a bubble and simmer for about 5-10 minutes until the liquid in the pan starts to thicken and the cranberries start to break down. (If needed, you can add a dash more water.) Then transfer to a bowl and set aside to cool slightly. Once cool, gently toss with the diced apples.
Preheat the oven to 400°F/ 204°C. Line 1 to 2 large baking sheets with parchment paper and set aside.
Remove each chilled dough disc from the fridge. Working with one disc at a time. roll the pie crust to about 1/8-inch thick. Using a 3.5-inch circle cookie cutter (or cup/ bowl) cut out as many circles from the pie crusts as you can, reroll any scrap pieces of dough as needed. You should get at least 16 circles. Transfer the cut-out pie crust circles to the baking sheets and set in the the fridge to chill a bit.
Make an egg wash by whisking the egg and tablespoon of milk together.
To fill the pies, start with one sheet pan and place about 2 tablespoons of filling in the center of 1/2 of the circles, being sure to leave the edges empty for sealing. (The other 1/2 of the circles will be the top crust.) Add one small cube of butter to the tops of the filling.
Brush the edges of the circles with a little egg wash. Place the top crust on top. Press your fingers all around the edges to seal, then crimp with a fork. It’s OK if some filling juice leaks out. Lightly brush the top of the pie crust with the heavy cream (or more egg wash if desired.) Sprinkle the tops with coarse or granulated sugar. (If placing a little leaf or other decoration on top, do this before sprinkling the sugar.) Cut 2 to 3 slits in the top of each pie for venting.
You can bake the pies immediately, though I recommend popping them in the freezer for a few minutes as they'll hold their shapes better when baking if they're cold.
Bake for about 20-25 minutes or until the pies are golden brown and the filling is bubbling a little. Remove from the oven and set aside to cool slightly before serving. Serve warm or at room temperature.
Baked pies can be stored in an airtight container at room temperature or in the refrigerator for 3 to 4 days.
*Assembled and unbaked hand pies can be covered tightly and refrigerated for up to 3 days or frozen for up to 3 months. If frozen, no need to thaw before baking, just add an extra couple minutes of bake time.
*Baked hand pies can be frozen for up to 3 months. Thaw in the refrigerator, then bring to room temperature before serving.
*Granny Smith and Honeycrisp or a combo of any other slightly tart/ sweet apples are my favorite to use for these.
*I recommend fresh over frozen cranberries. But if you use frozen, cook the juice downa little more.