Preheat oven to 425 degrees (F). Line a large baking sheet with parchment paper and set aside.

On a well floured surface, lay our pie dough and using a pumpkin shaped cookie cutter, cut out pie dough pieces. Grab scraps and roll out again to the same width and cut more pumpkin shaped pie dough pieces. Repeat the process until both pie crusts are used.

Lay half of the pumpkin pie dough pieces on the prepared baking sheet and place a lollipop stick half way up the dough. Save the other half of the dough pieces for the tops. Set aside while you make the filling.

In a medium bowl, combine the brown sugar and pumpkin puree and whisk together until combined. Add the pumpkin pie spice, salt, eggs and half and half and whisk well until combined.

Spoon a heaping teaspoon of the pumpkin pie filling on top of prepared dough on the baking sheet. Lay the other piece of dough symmetrically on top and using a fork, pinch the edges of the dough together to seal in the filling.

Pour the milk into a small bowl and use a pastry brush to brush the milk over the top of the crust. Sprinkle with coarse sugar.

Bake in the oven for 15 minutes or until tops of pies are golden brown.

Remove from oven and allow to cool on the baking sheet for five minutes. Transfer pies to a cooling rack by using a spatula to scoop the pies. Do not pick them up by the stick until completely cool. Allow to cool completely on wire rack and serve with with whipped cream.