Cream together shortening and sugar until creamy and smooth. 3 to 4 minutes.
Add the egg and beat until well incorporated, then add milk and vanilla and beat to combine.
Measure the flour, spices, salt, and baking powder into another bowl and sift it into the shortening mixture.
Gently mix until a uniform dough forms. Separate into 3 pieces in the following sizes: 1 ounce, 9 ounces, 12 ounces (or whatever remains).***
Add 1/2 teaspoon of green food powder dye into the 1 ounce portion and fold to combine until dough is uniform green color.
Add 1 tablespoon of orange dye to the 9 ounce portion of dough and blend until dough is a solid orange color. (See notes for liquid dye tips).
Shaping the Cookie Log
Lay parchment paper on a sheet of plastic wrap and roll out the plain dough into a 8 x 10 inch rectangle, about 1/4 inch thick. Trim the long edges to make an even straight line and set trimmings aside.
Form the orange dough into a 9 inch pumpkin log. When round and even, place near the bottom long edge of the dough rectangle, leaving about 1/2 inch on either end.
Use a butter knife to make a gentle indent along the top of the pumpkin log.
Roll the green dough into a thin, 9 inch rope. Place along the indent on the top of the pumpkins, gently pressing it down into the orange while pinching off the tip to create a triangular shape. Trim off excess if needed.
Use the white dough trimmings and line either side of the pumpkin stem to help it hold its shape during rolling.
When ready, carefully begin rolling the dough by lifting up the edge of the parchment and pulling gently away from yourself. Take your time and smooth the log as you go, keeping the roll tight.
Pull the parchment away and pinch the seam of the dough together gently. Fold in the edges of the dough like wrapping a Christmas present to close the log.
Wrap the plastic wrap tightly around the dough and roll it gently against a firm surface, like your clean counter to form a smooth log. You'll need to pause and press the ends in every few rolls to keep the log width uniform.
Chill for 30 minutes.
Baking Cookies
Preheat your oven to 350°F and line a baking sheet with parchment paper.
Remove cookies from fridge and slice with a sharp knife into 1/4 inch thick coins. You may need to gently reshape the cookies as you go to keep them round.
Place on cookie sheet 1 inch apart and bake for 7 to 9 minutes, or until edges are set and they no longer look wet.
Remove, allow to cool for 2 minutes on the pan, the move to a cooling rack. Enjoy!
Store cool leftovers in an airtight container for up to 4 days.
Notes
*Use up to 6 drops of liquid green food dye, and up to 6 yellow and 4 red drops of food dye to make the orange if you don't have the powdered dyes.