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Pumpkin Sandwich Cookies with Cinnamon Sugar and Chocolate Filling

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These Pumpkin Sandwich Cookies combine spiced buttery cookies with a smooth milk chocolate filling and a cinnamon sugar topping. Shaped like pumpkins and brushed with browned butter, they’re a fun and festive fall treat perfect for Halloween or cozy autumn days.

Ingredients

  • 1 1/2 cups (3 sticks) salted butter, softened
  • 1 1/4 cups light brown sugar, packed
  • 1 tbsp pure vanilla extract
  • 2 large eggs, at room temperature
  • 4 1/2 cups all-purpose flour
  • 1 tsp baking soda
  • 1 tsp cinnamon
  • 1/2 tsp ground ginger
  • 1/4 tsp nutmeg
  • 1/2 tsp salt
  • 12 oz milk chocolate, melted
  • 2 tbsp salted butter (for brushing)
  • 3 tbsp cinnamon sugar (for topping)

Instructions

  1. Cream softened butter, brown sugar, and vanilla until light and fluffy (3–5 minutes).
  2. Add eggs one at a time, beating well after each. Mix in flour, baking soda, cinnamon, ginger, nutmeg, and salt until a dough forms.
  3. Divide dough in half, shape into disks, and roll out each to 1/4-inch thickness on a floured surface.
  4. Use a pumpkin-shaped cookie cutter to cut out shapes. For half of the cookies, cut eyes and a mouth with a paring knife.
  5. Place cookies on a parchment-lined baking sheet and freeze for 15–20 minutes until firm. Re-roll scraps and repeat.
  6. Preheat oven to 350°F. Bake cookies for 8–12 minutes until lightly golden but still soft. Cool on the sheet for 5 minutes, then transfer to a wire rack.
  7. Melt 2 tbsp butter until lightly browned and fragrant. Brush over cookies with faces and sprinkle immediately with cinnamon sugar.
  8. Spread melted milk chocolate on the flat sides of plain cookies. Sandwich with the decorated tops and press gently.
  9. Serve immediately or let chocolate set before storing.

Notes

  • Use dark or white chocolate for a flavor variation.
  • Boost fall flavor with extra cinnamon or a dash of clove.
  • Mix finely chopped nuts into the dough for texture.
  • Replace vanilla with maple extract for richness.
  • Freeze shaped dough before baking to prevent spreading.

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