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Pumpkin Delight Cookies Recipe

4.8 from 135 reviews

Pumpkin Delight Cookies are a delicious seasonal treat combining soft spiced pumpkin filling sandwiched between tender, cinnamon- and molasses-infused cookies shaped like mini jack-o’-lanterns. These festive cookies bring cozy autumn flavors to your dessert plate with a charming Halloween twist, perfect for parties and family gatherings.

Ingredients

Scale

Pumpkin Filling

  • 15 oz canned pure pumpkin
  • 1 1/2 cups sugar
  • 2 tsp pumpkin pie spice
  • 2 tsp cinnamon
  • 1 tsp cornstarch
  • 3/4 cup apple juice

Cookie Dough

  • 12 tbsp butter, melted
  • 1 cup sugar
  • 1/4 cup molasses
  • 1 egg
  • 2 tsp baking soda
  • 1 tsp cinnamon
  • 1 tsp pumpkin pie spice
  • 1/4 tsp salt
  • 3 cups all-purpose flour

Instructions

  1. Make the pumpkin filling: In a medium saucepan, whisk together the canned pumpkin, 1 1/2 cups sugar, 2 tsp pumpkin pie spice, and 2 tsp cinnamon until fully blended. In a small bowl, mix the cornstarch and apple juice thoroughly to dissolve the cornstarch completely, ensuring there are no lumps.
  2. Cook the filling: Pour the cornstarch and apple juice mixture into the pumpkin mixture in the saucepan. Whisk everything together and cook over medium heat. Bring to a gentle boil, then reduce the heat and let it simmer for about 10 minutes, stirring occasionally to prevent sticking. Remove from heat and allow the filling to cool completely; it will thicken as it cools.
  3. Make the cookie dough: In a large mixing bowl, use a hand mixer to beat the melted butter and 1 cup sugar together for about 2–3 minutes until slightly thickened. Add the molasses and egg, continuing to beat until smooth and well combined.
  4. Add the dry ingredients: Mix in baking soda, 1 tsp cinnamon, 1 tsp pumpkin pie spice, salt, and flour with the hand mixer. Continue mixing until the dough comes together as a soft ball. If the dough is sticky, add more flour one tablespoon at a time until it can be handled without sticking.
  5. Chill and roll: Cover the dough and refrigerate for 30 minutes. Preheat the oven to 350°F (175°C). Lightly flour a surface, roll the dough to about 1/4 inch thick, and cut into pumpkin shapes using a cookie cutter. Flatten the tops slightly to enhance the pumpkin appearance.
  6. Create the pumpkin faces: For half of the cut cookies, carefully carve out jack-o’-lantern style faces using a small sharp knife, making triangle eyes and a mouth to resemble mini pumpkins.
  7. Assemble the cookies: Spoon about 1 tablespoon of cooled pumpkin filling onto each plain cookie base. Place a face cookie on top, aligning edges, and gently press around the edges to seal firm but not perfectly.
  8. Bake: Arrange the assembled cookies on parchment-lined baking sheets. Bake in the preheated oven for 10 to 13 minutes. Monitor the center areas near the faces to ensure even cooking. Let the cookies cool on the sheet for a few minutes, then transfer them to a wire rack to cool completely before serving.

Notes

  • Ensure the pumpkin filling is completely cooled before assembling to prevent dough sogginess.
  • If the dough is too sticky to handle, add flour sparingly; too much flour can make cookies tough.
  • Use parchment paper on baking sheets to prevent sticking and help with cleanup.
  • Cookies are best enjoyed within 2–3 days when stored in an airtight container.
  • For a festive touch, dust the cookies with powdered sugar before serving.

Keywords: pumpkin cookies, Halloween cookies, pumpkin pie spice, molasses cookies, autumn desserts, festive cookies, pumpkin filling