Pumpkin Chocolate Chip Pillow Cookies (gluten free option) #cookiemonth14

Pumpkin Chocolate Chip Pillow Cookies

Adapted from Nestle’s Very Best Baking
Makes 5 dozen cookies
Author Wendy Sondov themondaybox.com


  • 2 ¼ cups all-purpose whole wheat, or Bob’s Red Mill Gluten Free Baking Flour
  • 1 teaspoon baking powder
  • ½ teaspoon baking soda
  • ¼ teaspoon salt
  • 2 ½ teaspoons cinnamon
  • 1 cup unsalted butter room temperature
  • ½ cup granulated sugar
  • ½ cup brown sugar packed
  • 1 15 ounce can pumpkin puree
  • 2 large eggs
  • 2 teaspoons vanilla extract
  • 2 cups semi-sweet chocolate chips
  • For decorating:
  • 4 cups dark melting chocolate discs
  • sprinkles


  1. Preheat oven to 375˚F. Line a baking sheet with parchment paper.
  2. In a medium bowl, whisk together flour, baking powder, baking soda, salt, and cinnamon.
  3. In the bowl of an electric mixer, cream together butter and sugars. Beat in pumpkin, eggs and vanilla until incorporated.
  4. Gradually add flour mixture.
  5. Stir in chocolate chips.
  6. Scoop rounded tablespoon balls of dough onto prepared baking sheet, 2” apart.
  7. Bake for about 15 minutes or until the bottom edges are lightly browned.
  8. Cool for 5-10 minutes on the baking sheet before placing on a wire rack to cool completely.
  9. Decorating: Once completely cool, cookies can be drizzled or coated in melted chocolate. Melt the chocolate over a double boiler or in a microwave at 50% power.
  10. To drizzle, place cookies on a baking sheet lined with wax paper. Using a spoon or fork drizzle melted chocolate over cookies. Top with sprinkles while the chocolate is still wet. To coat, place cookies on a wire rack positioned over a wax paper lined baking sheet. Spoon melted chocolate over cookies. Top with sprinkles while the chocolate is still wet.
  11. Place the baking sheet of drizzled/coated cookies in the refrigerator for 5-10 minutes until the chocolate is set.
  12. Store cookies for 5-7 days in an airtight container at room temperature with wax paper between layers.

Packing Tips

Pumpkin Chocolate Chip Pillow Cookies should be mailed only in cool/cold weather care packages. In warm weather the chocolate coating will melt and the high moisture in the cookie would promote mold. For shipping, double wrap pairs of cookies (with bottoms together) in plastic wrap, then place in an airtight container.