Preheat oven to 375 degrees F.
Sift flour, cinnamon, baking powder and salt together twice. Cream butter and sugar in a stand mixer until light and fluffy. Combine egg, vanilla and almond extract and add to creamed mixture. Mix on medium speed until combined. Add sifted ingredients and mix only until combined; dough should be stiff.
Roll dough out between 2 sheets of parchment paper to a 12 by 9-inch rectangle, using 1 long sheet of parchment paper that is folded in half. Make sure that you roll out the dough evenly. Cut the edges off neatly with a bench scraper to even them. Place dough in the freezer until firm, about 15 minutes.
Mix together the canned pumpkin, pumpkin pie spice, and 1/4 cup brown sugar for filling.
Remove dough from freezer and peel back the top parchment paper. Thinly spread the pumpkin filling evenly over the dough. Don't spread too thickly; you should still be able to see the dough through the pumpkin slightly. If you don't use all of the filling, it is okay.
Starting at 1 end, roll up the ends in the same manner as a cake roll. Make sure that you keep it tight and even. If the dough cracks slightly, simply rub it together with your fingers. Wrap the roll in the parchment paper, seam side down, and place back in the freezer until firm, about 1 hour.
Slice cookies 1/4-inch thick and place onto a cookie sheet at least 1-inch apart. Sprinkle brown sugar on the tops of the cookies and rub it in with your fingers. Bake for 8 to 10 minutes, just until the edges are turning brown.
Serve cookies on a platter with a small bowl of whipped cream and nutmeg so that guests can make pumpkin pie pinwheel sandwiches. This makes it taste even more like pumpkin pie!
Recipe courtesy of Alisha Payton, Louisville, Kentucky