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Preheat the oven to 375°F. Line 2 large baking sheets with parchment paper.
On a floured surface, roll out dough about 1/8 inch thick.
Using a floured 3-inch round cookie cutter, cut out 20 circles, rerolling dough as needed.
Using a very sharp paring knife, cut out jack-o’-lantern faces in half of the dough circles. (Alternatively, roll out each portion of the dough into 10x16-inch rectangles and cut out 10 rectangles from each, rerolling dough as needed. If making these larger pies, bump the pumpkin purée measurement to 1 cup and brown sugar to 3 tablespoons.)
Bake until golden brown, about 20 minutes. Let cool slightly on the baking sheets before serving.
Hand pies will keep in an airtight container at room temperature for up to 3 days.