Smooth and velvety cream cheese frosting sandwiched between two soft, chewy, thick, and rich pumpkin cookies -- PumpkinWhoopiePies are the ultimate fall treat!
PREP: Prepare a large sheet pan by lining with parchment paper or a Silpat liner (very important to avoid burned bottoms on these cookies). Preheat oven to 350 degrees F.
DRY INGREDIENTS: Add flour, baking soda, baking powder, cinnamon, pumpkin pie spice, and salt to a large bowl; whisk to combine and set aside.
WETINGREDIENTS: In a medium bowl, cream together the butter, white sugar, and brown sugar until smooth and creamy. Add 1 cup pumpkin, the egg, and vanilla. Beat until the mixture is creamy. Add in the dry ingredients and mix until JUST combined. Avoid overmixing, as it will create dense cookies.
OPTIONAL -- CHILL DOUGH: Cover tightly and chill the dough for 30 minutes up to 10 hours. Chilling is not necessary but it makes the dough much easier to work with and intensifies flavors.
ROLL COOKIE BALLS: Use a 1 tablespoon measuring spoon to scoop out balls of dough. Each cookie should be about 1 tablespoon in size. Once dough is in the tablespoon measuring spoon, use a small spoon to scoop it onto the lined sheet pan. Try to smooth or round the balls, but it's okay if they're a bit bumpy; this dough is difficult to work with. Leave 2 inches between each cookie (I only bake 8-10 cookies at a time) and flatten the balls of dough slightly. (This batter is wetter than normal cookie dough so don't be alarmed that you can't roll out balls of dough; chill in the fridge for additional time if needed to make it easier to get cookie dough balls on a tray).
BAKE: Bake for 8-13 minutes (9-10 minutes is perfect for my oven) watching carefully to avoid over-baking. We like these slightly under-baked and soft, but the tops shouldn't be shiny or wet looking at all. Remove and allow cookies to stand for 3-5 minutes on the sheet pan before removing to a wire cooling rack to finish cooling.
FROSTING: Meanwhile, make the frosting. In a stand mixer fitted with the whisk attachment (or a large bowl and a hand mixer), beat the softened (not melted) cream cheese and butter until creamy for about 2 minutes at medium-high speed. Add the powdered sugar, salt, and vanilla. Beat until everything is combined and the frosting is soft and creamy. Avoid over-beating the mixture or you'll get whipped frosting.
FROSTCOOKIES: Generously frost half of the cooled cookies. Sandwich the other half of the cookies on top.
STORAGE: Do not store the cookies in plastic containers. Store on plates loosely covered with foil in the fridge. Best eaten same day or within 1-2 days. After that, they soften too much and the texture degrades. Freeze unbaked cookie dough balls for up to 3 months; bake straight from freezer for an additional 1-3 minutes.
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Notes
Note 1: If you press a measuring cup into a bag of flour, you will pack in way too much flour; use a spoon to scoop it into a measuring cup and then level the top with the back of a table knife.