Preheat your oven to 400°F, placing the rack in the middle. Line a baking sheet with parchment paper and spray it with nonstick spray.
Mix pumpkin puree, brown sugar, salt, and pumpkin pie spice in a bowl.
Transfer the mixture to a saucepan and cook over medium-high heat, stirring until it thickens, about 6-8 minutes.
Remove from heat, then stir in cream cheese, half of the beaten eggs, and vanilla until smooth. Set aside.
Roll out the chilled pie crust and cut out pumpkin shapes. Place them on the prepared parchment.
Insert a popsicle stick into the center of each pumpkin shape, with the stick halfway up and the long end hanging out.
Add a spoonful of filling into each pumpkin cutout.
Cut small triangles for eyes and a mouth to create a jack-o'-lantern face on the pumpkin tops.
Place the tops on the filled pumpkins, pressing edges with a fork to seal.
Brush the tops with the remaining beaten egg and sprinkle with turbinado sugar.
Bake for 12-15 minutes until golden. Cool on the sheet, then display in a jar of sugar for a festive look.