1. Sift together flour, baking powder, cinnamon, pumpkin spice, and salt. Set aside.

2. In a large bowl add the butter and sugar and beat with an electric hand mixer (or stand mixer) until light and fluffy. Add the egg and milk and beat to combine, make sure it is thoroughly incorporated.

3. With the mixer on low, add the flour a little at a time until it starts to pull away from the sides and forms a dough. Divide the dough in half and shape into discs. Wrap with plastic or wax paper and chill for 2 hours.

4. Preheat oven to 375 degrees Fahrenheit. Line 3 -4 sheet pans with parchment paper and set aside. 

5. Dust a workspace with powdered sugar. Remove one portion of dough at a time from the refrigerator and roll each portion out onto the sugared work surface until it is 1/4 inch thick. Use a 1 + 1/2 in size cookie cutter to cut shapes out of the dough.

*Do not discard the scraps. Rework the scraps back into a disc of dough and roll out again into 1/4 inch thick sheet. Cut out another batch of cookies. I do not recommend rolling the dough out a third time as the butter heats up and the gluten gets worked. 

6. Place the cookies approx. 1 inch apart onto the lined sheet pans. Bake for 12- 15 minutes, rotating halfway through, until the edges and bottom of cookies have just started to brown. Let the cookies cool on the sheet pan for 1-2 minutes, then transfer to a wire rack to cool completely. 

7. To make the cream filling combine the shortening, extract, and syrup in a large mixing bowl and beat with an electric hand mixer until combined thoroughly. Beat mixture for 2 minutes on medium speed. Add the powdered sugar and beat on low until combined. Change speed to medium/high and whip filling until fluffy. 

8. Split the batch of cookies in half between two sheet pans. Flip one batch of the cookies over so that the flat bottom is now facing up. Leave the other half with the flat bottom side down. Fill a pastry bag with the maple filling. *If you do not have a pastry bag you can use a small offset spatula.

9. Pipe or frost about a teaspoon of filling onto each cookie that has the flat bottom side facing up. Top with the remaining cookies that have the flat side down. Gently press the cookies together so the cookies form a sandwich and stay together. Serve immediately, or store in an airtight container for 2 days. 

*This recipe makes a good amount of frosting, you can halve it, or store the extra frosting in the refrigerator to use on more cookies in the future as shortening has an incredibly long shelf life. Just be sure to allow the frosting to come completely to room temperature so it can be piped or spread easily.