Use a hand-mixer or stand mixer to cream the butter and brown sugar together in a large bowl.
Beat in the egg, vanilla extract, and orange zest until combined.
In a separate medium bowl, whisk together the flour, allspice, ginger, cinnamon, and salt.
Add the dry ingredients into the wet ingredients a little at a time, beating well after each addition and scraping down the sides of the bowl as needed, until all ingredients are completely combined.
Turn the cookie dough out of the bowl and onto the prepared piece of plastic wrap. Wrap dough completely in plastic and freeze for 30 minutes, or refrigerate overnight.
Sprinkle your clean work surface and rolling pin with powdered sugar. Roll the chilled dough to a ¼ inch thick, then use a cookie cutter to cut out your cookies.
Place cookies about an inch apart on the prepared baking sheets, then refrigerate the baking sheets for about 10 minutes to chill the dough.
Gather the remaining scraps of dough and repeat the sprinkling, rolling, cookie cutting, and chilling process again until all the dough is used up.
Bake Winter Wishing Cookies at 350F for 8-10 minutes, or until the bottoms of the cookies are just starting to brown.
Remove the baking sheets to a wire rack and let Winter Wishing Cookies cool on the sheets for 5 minutes.
Transfer Winter Wishing Cookies to wire rack to finish cooling. Sprinkle cooled cookies with powdered sugar for decoration (optional).