Preheat oven to 375 degrees F and line a baking sheet with parchment paper.
In a bowl or mixer, combine pumpkin puree, maple syrup, pumpkin pie spice, and vanilla.
Roll out the pie dough 1/4-inch thick on a floured surface. Use a pumpkin cookie cutter to cut out approximately 20 pumpkins.
Place a heaping spoonful of filling in the center of half the pumpkins and lightly spread across, avoiding the edges.
Top with the remaining pumpkin shapes and lightly press the edges of the dough around each pumpkin to seal.
Place the cookies on your prepared baking sheet. Bake for 15 minutes, or until golden brown.
Let the baked pop-tarts cool on the pan for a few minutes, then transfer to a wire rack to cool before glazing.
Mix cinnamon glaze ingredients and top each pop tart (optional)
Enjoy!