To make the cookies: Preheat the oven to 350°F (177°C). Line two to three large baking sheets with parchment paper or silicone baking mats and set aside.
In a large mixing bowl, whisk together the flour, baking powder, and salt. Set aside.
3 cups all-purpose flour, 2 teaspoons baking powder, ½ teaspoon salt
In a separate large mixing bowl using an electric mixer, mix the shortening and sugar together for 1 to 2 minutes or until well combined. Add the egg, milk, and vanilla extract and mix until fully combined, making sure to stop and scrape down the sides of the bowl as needed.
1 cup vegetable shortening, 1 cup granulated sugar, 1 large egg, 2 tablespoons whole milk, 2 teaspoons pure vanilla extract
Add the dry ingredients and mix until fully combined. The mixture will be a little crumbly at first, but it will come together as you continue mixing it. Once the dough comes together, use your hands to form it into a ball.
Divide the dough in half. Lightly flour a piece of parchment paper, add half of the dough, top with another piece of parchment paper, and roll the dough to ¼-inch thick between both pieces of parchment paper. Repeat with the other half of the dough between two separate pieces of parchment paper. (This dough doesn't require any dough chilling, but if you prefer colder dough so that it's easier to work with you can place both pieces of rolled out dough between the parchment paper on a baking sheet and refrigerate for 30 minutes to one hour.)
Peel off the top layer of parchment paper. Using 3 to 4 inch Halloween cookie cutters, cut the cookie dough into shapes and place them onto the prepared baking sheets, making sure to leave a little room between each one. If the cut out dough is difficult to pick up, lightly flour a thin spatula and use that to transfer the cut out cookies to the baking sheet. Re-roll any scrap pieces of dough between the parchment paper and continue cutting out shapes. Repeat with the other sheet of cookie dough.
Bake for 10 to 13 minutes or until the tops of the cookies are set and the bottom edges are lightly browned. I prefer to bake mine between 12 to 13 minutes, so they’re slightly crisper - the icing will soften them some!
Remove from the oven and allow to cool on the baking sheets for 5 to 10 minutes, then transfer the cookies to a wire rack to cool completely.
Prepare the icing: For these cookies, I used my royal icing recipe and beat it to a medium consistency so I could use it to outline and flood the cookies all at once. If you want an easier icing, my easy sugar cookie icing will work too. If you use my easy sugar cookie icing, I recommend making it thick enough so you can use it to outline and flood the cookies all at once.
Divide and color the icing: If you plan to use a few different colors of icing, divide the icing between several different bowls and add gel food coloring. I divided about ¾ of my icing between three larger bowls, left one white, tinted one with black, and the other one with orange gel food coloring. I divided the last ¼ of the icing between two smaller bowls and tinted one with yellow and the other with green food coloring. At this point I also recommend checking the consistency of your icing again. If the icing is too thick, you can add a little water to thin it out. If it’s too thin, you can add a bit more powdered sugar to thicken it.
Gel food coloring
Once all of the icing is colored and prepared, distribute it between piping bags with your desired piping tip. I personally prefer to use the Wilton #3 piping tip! If you still have some icing in bowls that you are not using, make sure to cover it with a damp paper towel until you’re ready to use it to prevent it from hardening.
To decorate the cookies: Outline each cookie with the icing, then fill the cookie with a thin layer of icing. Use a toothpick or scribe to move the icing around and fill in any empty spots. If needed, gently tap or shake the cookie to help the icing settle in a smooth layer. If adding any sprinkles, go ahead and add them as soon as you ice each cookie. Here’s how I decorated my cookies:Bat Cookies: Outline and fill them with black icing, wait until the icing dries some, then add the detail to the wings and the eyes.Witches Hat: Outline and fill the black portions of the hat, then add the green stripe across it. Wait for the icing to harden some before adding the yellow buckle and sprinkles.Ghost: Outline and fill with white icing, then add the black eyes and mouth while the icing is still wet (this allows them to blend together!).Pumpkin: Start by outlining and filling in the orange parts on each side, then go back and fill in the middle portion. Add the green top and any leaf decorations, if you prefer. You can also just outline and fill the cookie all at once with orange icing, then add some black details for jack-o-lantern cookies.Candy Corn: Outline and fill each color, starting with white at the smaller end, orange in the middle, and yellow at the larger end.
Once you’ve iced all of the cookies let them dry at room temperature for several hours or until the icing has hardened. The amount of time this can take will vary depending on how large your cookies are, how much icing you’re using, and the amount of airflow. To be safe, I prefer to let my cookies dry overnight before stacking them.
Notes
Storage Instructions: Cookies may be stored in an airtight container at room temperature for up to one week.Freezing Instructions: Cookies will freeze well for up to 3 months. Thaw to room temperature before serving.