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

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

  1. 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.
  2. Chill dough – Wrap dough in plastic and chill for 30 minutes.
  3. 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.
  4. Bake – Place on parchment-lined baking sheet and bake at 350°F (175°C) for 8–10 minutes. Let cool.
  5. Add chocolate filling – Spread melted milk chocolate on the solid pumpkin cookies. Top with a face-carved cookie and gently press to sandwich together.
  6. 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.

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