Using a stand mixer, cream the softened butter on low for 1 minute. Scrap off sides. Add brown sugar and cream together with the butter for approximately 2 minutes, until the mixture is light and fluffy.
Slowly add in the egg, maple syrup, and vanilla and beat until well blended (about 1 minute).
In a separate large bowl, whisk together the flour, baking powder, 1/4 teaspoon ground cinnamon, and salt.
Slowly add dry mixture to the wet mixture and beat until just blended. The dough will be soft. Chill just slightly in the fridge for 5-10 minutes, when it's thick enough to create shapes using the cookie press. Still too soft? Chill for another 5-10 minutes until it's ready to press through (but make sure it's not fully chilled!).
Outfit your cookie press with your favorite fall shape (I made leaves, spiders, and pumpkins), and press dough into the cookie press container following the manufacturer instructions. Press out shaped dough onto an ungreased, cold cookie sheet (or at least at room temperature; if it's warm, place the sheet in the refrigerator for a couple of minutes).
Sprinkle cinnamon sugar mixture over each cookie.
Bake at 350 degrees for 8-10 minutes, just until the sides and bottoms of each cookie are light brown.
If dough is still too soft after slightly chilling it, return it to the refrigerator and chill further, in 5-10 minute increments until the consistency comes out nicely through the cookie press. You don't want it to be fully chilled; then it won't go through the press at all. You just want it to hold shape while it goes through the press shapes.Remember: the first push through the cookie press is meant to get the dough through an even amount going forward, and usually doesn't come out ready for baking.
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