Cookies & BarsNo. 9532 · The 2026 edition
Milk Chocolate Stuffed Jack-O'-Lantern Cookies
These milk chocolate stuffed jack-o'-lantern cookies are a spooky, delicious treat with a hidden chocolate surprise!
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These festive cookies feature a soft pumpkin-shaped cookie sandwich filled with melted milk chocolate. The top cookie is brushed with browned butter and cinnamon sugar, then baked until lightly golden. Perfect for Halloween, they're easy to make and sure to impress.
Ingredients
Directions
- In a large bowl, beat the softened butter, brown sugar, and vanilla together until light and fluffy, about 3–5 minutes. Beat in the eggs one at a time until fully combined. Add the flour, baking soda, cinnamon, ginger, nutmeg, and salt, and mix until a ball of dough forms.
- Dust your work surface generously with flour. Split the dough in half and shape each half into a disk. Roll one disk to 1/4-inch thickness, using enough flour to prevent sticking. Cut out pumpkin shapes with a pumpkin cookie cutter and transfer to a parchment-lined baking sheet. Using a small knife or cookie cutter, carve eyes and a mouth into half of the cookies. Cover the sheet and freeze for 15–20 minutes until firm. Reroll the scraps and repeat with the remaining dough disk.
- Preheat oven to 350°F. Bake the cookies on the middle rack for 8–12 minutes for soft cookies, or just until lightly golden. Do not overbake. Let them cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
- In a medium pot, melt the 2 tablespoons of butter over medium heat, stirring often, until it turns light brown and smells toasted, about 2–3 minutes. Remove from heat and let cool for 5 minutes. Brush the browned butter over the top half of each cookie, then sprinkle with cinnamon sugar.
- To assemble, spread a layer of melted milk chocolate over the flat (face-less) halves of the cookies. Place a face-topped cookie on top and gently press to stick. Serve right away, or let the chocolate set, then store in an airtight container for up to 3 days.
Per serving
- 254.0 calories
More photos
Photos hosted by halfbakedharvest.com.