Preheat your oven to 180°C (350°F) and line baking sheets with parchment paper.
In a large bowl, whisk together the flour, baking soda, cinnamon, ginger, and salt until evenly combined.
In a separate bowl, cream together the softened butter and brown sugar using an electric mixer or whisk until the mixture is fluffy and light, about 2 minutes. You should see it turn paler and feel a slight resistance when mixing.
Add the egg to the butter mixture and beat until fully incorporated, then stir in the pumpkin puree and vanilla extract until the batter looks smooth and slightly thickened.
Gradually add the dry ingredients to the wet mixture, mixing just until everything is combined. The dough will be soft but scoopable.
Using a spoon or cookie scoop, drop dollops of dough onto the prepared baking sheets, spacing them about 2 inches apart to allow for spreading.
Bake in the preheated oven for 12-14 minutes, until the edges are golden and the tops are set with a slight dome. The cookies should feel firm but still soft to the touch.
Remove the baking sheets from the oven and let the cookies cool on the sheets for about 5 minutes, then transfer them to a wire rack to cool completely. The cookies will firm up as they cool.
While the cookies cool, prepare the filling by mixing softened cream cheese or mascarpone with powdered sugar until smooth and creamy. Chill the filling briefly if it’s too soft to spread.
Once the cookies are cool, spread a generous layer of the creamy filling onto the flat side of one cookie, then top with a second cookie to form a sandwich. Gently press to spread the filling evenly to the edges.
Repeat with the remaining cookies and filling, then enjoy your soft, spicy pumpkin whoopie pies—perfect for sharing or indulging on a cozy day.
