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American·Dessert

Halloween Pumpkin Whoopie Pies

These tender pumpkin-spiced cookie sandwiches feature a rich cream cheese filling and festive, hand-piped Halloween decorations. While the spooky designs are optional, the light, cake-like texture and classic autumn flavors make these a standout seasonal treat.

Prep

30m

Cook

18m

Total

60m

Serves

10

Method

  1. 01

    In a mixing bowl, whisk together the flour, salt, baking powder, baking soda, cinnamon, ground ginger, and ground cloves for about 30 seconds until evenly combined.

    Step 1
    Watch · 0:25
  2. 02

    In a separate large bowl, whisk together the pumpkin puree, brown sugar, egg, and vegetable oil until perfectly smooth. Stir in a few drops of orange food coloring if using, then whisk in the dry ingredients to form a loose cookie batter.

    Step 2
    Watch · 0:56
  3. 03

    Using a sorbet scoop or tablespoon, portion half of the batter onto a lined sheet pan to serve as the bottom cookies. Use a wet finger to lightly flatten and round the shapes. For the remaining batter, mix in a generous amount of brown or black food coloring and transfer to a piping bag with a fine tip.

    Step 3
    Watch · 2:05
  4. 04

    Portion the remaining batter onto a second lined pan for the top cookies. Pipe Halloween designs—such as spiderwebs or jack-o'-lantern faces—directly onto the raw batter. Transfer to the upper center of a 350°F (175°C) oven and bake for about 18 minutes until the edges are barely golden brown.

    Step 4
    Watch · 3:05
  5. 05

    Let the cookies cool on the pan for 10-15 minutes before moving them to a cooling rack. While they cool, prepare the filling by mixing the cream cheese, butter, milk, vanilla, and powdered sugar with an electric mixer until smooth. Chill the frosting briefly to firm it up.

    Step 5
    Watch · 4:00
  6. 06

    To assemble, pipe a generous amount of filling onto the flat side of a plain bottom cookie. Place a decorated top cookie over the filling and squeeze gently until the frosting reaches the edges. Refrigerate the assembled whoopie pies before serving for the best texture and flavor.

    Step 6
    Watch · 6:00

From Chef John

  • “You guys are after all the coastal elites of these Amish treats.”
  • “I think we'd all agree cookie problems aren't like regular problems.”
  • “Besides looking super cool and terrifyingly adorable, the cookie itself is very light and tender and tastes like pumpkin pie.”