These pumpkin whoopie pies turn simple pantry staples into pillowy, cakey cookies sandwiched around a tangy cream cheese filling. Every bite starts with a tender pumpkin cookie full of cinnamon and pumpkin pie spice, then melts into a velvety, lightly sweet center. They are easy enough for beginners, yet the results look and taste like they came from a bakery.
Preheat oven to 350°F (175°C) and line two baking sheets with parchment paper.
Whisk together flour, baking powder, baking soda, pumpkin pie spice, cinnamon, and salt in a medium bowl.
Beat softened butter and brown sugar on medium speed for 2 to 3 minutes until pale, light, and fluffy, scraping down the bowl as needed.
Beat in pumpkin puree, egg, and vanilla on low speed for about 1 minute until combined, being careful not to overmix.
Add the dry ingredients to the wet ingredients a little at a time on low speed, mixing just until the flour disappears and the batter is thick and slightly sticky.
Drop tablespoon-sized mounds of batter about 2 inches apart onto the prepared baking sheets, aiming for 24 cookies total. Bake for 10 to 12 minutes until edges are set and tops spring back. Cool 5 minutes on the sheets, then transfer to a rack to cool completely.
Beat cream cheese and butter for about 2 minutes until smooth, then gradually add powdered sugar and vanilla, beating until fluffy and spreadable.
Spread or pipe 1 to 2 tablespoons of filling onto the flat side of one cooled cookie, top with a second cookie flat side down, and press gently until the filling reaches the edges. Repeat to make 12 whoopie pies.
Notes
Use room-temperature butter and cream cheese for smoother mixing.
Measure flour by spooning it into the measuring cup and leveling it off to avoid dense cookies.
Do not skip the parchment paper so the cookies release easily.
Chill the assembled whoopie pies for 30 minutes to help the filling set.
Bake one sheet at a time for even heat distribution.
Swap the cream cheese filling for a maple frosting made with maple syrup for a variation.
Add 1/2 cup mini chocolate chips to the batter for a chocolatey kick.
Store in an airtight container in the refrigerator for up to 5 days.
Freeze assembled whoopie pies wrapped individually in plastic wrap for up to 2 months; thaw in the fridge overnight or at room temperature for about an hour.
Let them sit at room temperature for 10 to 15 minutes before serving if you prefer a softer texture.