Preheat the oven to 350 degrees F (175 degrees C). Line 4 baking sheets with parchment paper.

Cream brown sugar and butter together using an electric mixer. Add pumpkin, 2 tablespoons maple syrup, and egg; mix well.

Sift flour, baking powder, baking soda, cinnamon, and salt together in another bowl. Mix into pumpkin mixture. Stir in raisins.

Drop batter by teaspoonfuls onto the prepared baking sheets.

Bake in the preheated oven until edges are golden, 11 to 13 minutes. Remove from the oven and let cool on the baking sheet for 1 minute before removing to a wire rack to cool, 8 to 10 minutes more.

Mix confectioners' sugar and 1/4 cup maple syrup for icing together in a bowl. Drizzle onto cooled cookies.