Halloween Cookie Recipes: Milk Chocolate Stuffed Jack-O’-Lantern Cookies

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If you’re looking for the ultimate Halloween cookie recipe, these Milk Chocolate Stuffed Jack-O’-Lantern Cookies are guaranteed to steal the show. Buttery sugar cookie dough is shaped into pumpkins, carved with fun jack-o’-lantern faces, and filled with rich milk chocolate for a gooey surprise inside.
They’re festive, fun to make with kids, and the perfect addition to your Halloween dessert table. Each bite combines soft cookie layers with a creamy chocolate center—spooky, cute, and absolutely delicious.
Why You’ll Love These Jack-O’-Lantern Cookies
- Festive & creative – shaped like carved pumpkins.
- Chocolate surprise – stuffed with melty milk chocolate.
- Fun for kids – little ones can help cut out the faces.
- Perfect party treat – makes a standout Halloween dessert.
What Are Jack-O’-Lantern Cookies?
These Jack-O’-Lantern Cookies are made from sugar cookie dough cut into pumpkin shapes. Some are carved with spooky faces to look like jack-o’-lanterns, while others serve as the solid backing. Sandwiched together with melted milk chocolate inside, they bake into a fun, festive Halloween cookie recipe that’s equal parts decorative and delicious.
Ingredients (Exact)
- 2 ½ cups all-purpose flour
- 1 tsp baking powder
- ½ tsp salt
- ¾ cup unsalted butter (softened)
- 1 cup sugar
- 1 large egg
- 1 tsp vanilla extract
- ½ tsp pumpkin pie spice (optional for flavor)
- 6 oz milk chocolate (bars or chips, melted)

How to Make Milk Chocolate Stuffed Jack-O’-Lantern Cookies
- Make cookie dough – In a bowl, whisk flour, baking powder, salt, and pumpkin pie spice. In another bowl, beat butter and sugar until creamy. Add egg and vanilla. Slowly mix in dry ingredients until dough forms.
- Chill dough – Wrap dough in plastic and chill for 30 minutes.
- Cut shapes – Roll dough ¼ inch thick. Use a pumpkin cookie cutter to cut out even shapes. On half, carve jack-o’-lantern faces with a small knife.
- Bake – Place on parchment-lined baking sheet and bake at 350°F (175°C) for 8–10 minutes. Let cool.
- Add chocolate filling – Spread melted milk chocolate on the solid pumpkin cookies. Top with a face-carved cookie and gently press to sandwich together.
- Set & serve – Let chocolate set before serving.

Tips & Variations
- Different fillings – try dark chocolate, Nutella, or peanut butter cups.
- Add color – tint dough with orange food coloring for extra pumpkin vibes.
- Gluten-free option – swap flour for a 1:1 gluten-free blend.
FAQs
Can I make the dough ahead of time?
Yes! Store in the fridge for up to 2 days before baking.
Do these cookies freeze well?
Absolutely—freeze unfilled cookies for up to 2 months. Just add chocolate after thawing.
What if I don’t have pumpkin cutters?
You can use a round cutter and carve pumpkin faces freehand.
Conclusion
These Milk Chocolate Stuffed Jack-O’-Lantern Cookies are the perfect Halloween cookie recipe—spooky, festive, and irresistibly delicious. Whether for a party, school event, or cozy family night, they’ll add sweetness and fun to your Halloween celebration.

