Pilgrim Hat Chocolate Pumpkin Cookie Cups

Pilgrim Hat Chocolate Pumpkin Cookie Cups


These Pilgrim Hat Chocolate Pumpkin Cookie Cups are a just as tasty as they are adorable. Decorate chocolate cookie cups with a modeling chocolate or fondant belt and belt buckle to look like a pilgrim’s hat then fill the cups with creamy pumpkin mousse to make a delicious and festive Thanksgiving dessert.


  1. Chocolate Cookie Cups

    • 10 tablespoons unsalted butter softened slightly
    • 3/4 cups [brand: name] Extra Fine Granulated Sugar
    • 1/2 teaspoons vanilla
    • 1 egg
    • 1 3/4 cup all-purpose flour*
    • 1/3 cup cocoa powder
    • 1/4 teaspoon baking powder
    • 1/2 teaspoon salt
  2. Decorations

    • 2 ounces white modeling chocolate or fondant
    • Edible gold luster dust
    • Clear piping gel, frosting, or melted chocolate
  3. Pumpkin Mousse


  • Chocolate Cookie Cups
  • Decorations *See ingredients
  • Pumpkin Mousse
  • Mixing Bowl
  • Muffin Cups
  • Non-Stick Baking Spray
  • Wooden Pie Stamper or Wooden Spoon
  • Pastry piping bag & tips



  1. Prepare Chocolate Cookies: Spray 14 two-inch muffin cups with non-stick baking spray.
  2. In a large mixing bowl, combine butter and sugar. Cream until light and fluffy. Then mix in vanilla and egg.
  3. In a separate bowl, combine flour, cocoa powder, baking powder, and salt.
  4. Add to butter mixture and mix until just combined.
  5. Spoon two tablespoons of dough into one muffin cup.
  6. Press dough into bottom and up sides of the cup. Repeat filling 14 muffin cups with cookie dough.
  7. Freeze pan(s) for 30 minutes.
  8. Meanwhile, preheat oven to 350°F. Bake cookie cups for 16-18 minutes, rotating pans midway through the baking cycle.
  9. Remove pans from oven and if needed use a wooden pie stamper or back of a wooden spoon to flatten out bottoms of cookie cups.
  10. Let cool in pans for about 15 minutes then gently remove from pan.
  11. For decorations, roll white modeling chocolate or fondant out to about 1/16-inch thickness. Cut out fourteen 1/8x8-inch long strips and 1/4-inch squares.
  12. Brush gold luster dust over squares. Wrap a strip around each cookie cup attaching it using clear piping gel, frosting, or melted chocolate. Attach one square belt buckle opposite the seam.
  13. Prepare Pumpkin Mousse: Beat cream cheese until smooth and creamy. Add powdered sugar and vanilla extract and beat until light and fluffy.
  14. Mix in pumpkin puree and pumpkin pie spice then fold in whipped topping.
  15. Store mousse in the refrigerator until ready to serve, then fill each cookie cup with mousse. 
  16. The mousse will look really pretty if you pipe a big swirl of it into the cups. To do so, put a large star shaped frosting tip into an 18-inch pastry bag. Fill the bag with pumpkin mousse, then pipe a swirl of mousse into each cup.
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