Five little pumpkins sitting on a gate, one fell off...onto my plate! These oh-so-buttery and sparkly pumpkin-shaped cookies are filled with a rich and creamy cinnamon-chocolate ganache. They are the perfect Halloween favor or centerpiece for your fall gatherings.
For the cookies: Cream the butter and granulated sugar in a stand mixer fitted with the paddle attachment on medium-high speed until light and fluffy, about 3 minutes. Add the vanilla and egg and mix on medium speed to combine, scraping down the sides of the bowl with a rubber spatula as needed, about 2 minutes. Add the flour and salt in 2 batches and mix on low speed, scraping down the sides of the bowl as needed, until the flour is just incorporated (be sure not to overmix), 2 to 3 minutes.
Divide the dough in half and place each half on a large piece of parchment. Top each piece of dough with a second piece of parchment. Roll out the dough to about 1/4 inch thick. Stack the rolled dough on a baking sheet and refrigerate until chilled and firm to the touch, about 1 hour.
Position oven racks in the top and bottom thirds of the oven and preheat to 375 degrees F. Line 2 baking sheets with parchment. Put the cinnamon in a small bowl.
Carefully peel off the top sheets of parchment from the dough. Cut out the cookies using a 3-inch pumpkin-shaped cookie cutter. Transfer the cookies to the prepared baking sheets, spacing them 2 inches apart. Sprinkle half the cookies with about 1 teaspoon orange sanding sugar per cookie, leaving the stems of the pumpkins without sprinkles. Using your finger, dab some of the cinnamon on the stems of the decorated cookies. Refrigerate the cookies until firm, about 15 minutes.
Bake the cookies, rotating the baking sheets from top to bottom and front to back halfway through, until lightly golden around the edges, 10 to 12 minutes. Allow the cookies to cool for 5 minutes before transferring them to a cooling rack to cool completely.
For the ganache: Meanwhile, combine the chocolate chips and cinnamon, if using, in a medium heat-safe bowl.
Heat the cream in a small saucepan until it just comes to a simmer. Pour the cream over the chocolate chip mixture and allow it to sit for about 10 minutes. Whisk, starting in the center and working outwards, until the mixture is lump-free. (If lumps remain, microwave the mixture in 20-second intervals, stirring in between each, until no lumps remain.) Cover the ganache with plastic wrap and refrigerate until thickened and spreadable, about 30 minutes.
Spread the ganache on the undecorated cookies (about a generous tablespoon each) and sandwich with the decorated ones.
When measuring flour, we spoon into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)