25-Minute Milk Chocolate Stuffed Jack-O’-Lantern Cookies
Festive pumpkin-shaped cookies stuffed with creamy milk chocolate and topped with a cinnamon-sugar coating. Perfect for Halloween celebrations and fall gatherings.
- Prep Time: 30 minutes
- Cook Time: 15 minutes
- Total Time: 45 minutes
- Yield: 30 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Ingredients
For the Cookies:
3 sticks (1 ½ cups) salted butter, softened
1 ¼ cups packed light brown sugar
1 tbsp pure vanilla extract
2 large eggs, at room temperature
4 ½ cups all-purpose flour
1 tsp baking soda
1 tsp ground cinnamon
½ tsp ground ginger
¼ tsp ground nutmeg
½ tsp salt
12 oz milk chocolate (bars or melting wafers), melted
For the Cinnamon Sugar Coating:
2 tbsp salted butter
3 tbsp cinnamon sugar
Instructions
1. In a large bowl, cream together butter, brown sugar, and vanilla until light and fluffy, about 3-5 minutes.
2. Add the eggs one at a time, mixing well after each.
3. In a separate bowl, whisk together flour, baking soda, cinnamon, ginger, nutmeg, and salt. Gradually mix into wet ingredients until dough forms.
4. Divide dough into two disks, wrap in plastic, and refrigerate for 30 minutes.
5. Preheat oven to 350°F (175°C) and line baking sheets with parchment.
6. Roll dough to ¼-inch thickness. Cut pumpkin shapes with cookie cutter. Cut faces into half of them.
7. Place cut-out cookies on sheets and freeze for 15-20 minutes.
8. Bake 8-12 minutes until edges are golden. Cool 5 minutes, then transfer to rack.
9. Melt milk chocolate in microwave or double boiler.
10. Brown 2 tbsp butter, cool slightly, and brush over face cookies. Sprinkle with cinnamon sugar.
11. Spread melted chocolate on flat sides of plain cookies. Top with face cookies to sandwich.
12. Store in airtight container at room temperature up to 3 days.
Notes
For best results, chill dough to help cut clean shapes. Use high-quality milk chocolate for a smoother filling. These cookies hold shape well when chilled before baking.