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Milk Chocolate Stuffed Jack-O-Lantern Cookies

Milk Chocolate Stuffed Jack-O-Lantern Cookies

The Crispy Chef
These Halloween cookies are soft, chewy, and stuffed with melty milk chocolate centers. They're spiced just right and decorated with jack-o-lantern faces for a festive look that doesn't sacrifice flavor.
Prep Time 40 minutes
Cook Time 12 minutes
Total Time 52 minutes
Course Dessert
Cuisine Halloween
Servings 24 cookies
Calories 210 kcal

Equipment

  • Two baking sheets
  • Parchment paper or silicone mats
  • Cookie scoop (2 tbsp size)
  • Small piping bag or plastic bag for decorating
  • Wire cooling rack
  • Saucepan (light-colored) for browning butter

Ingredients
  

  • 2 3/4 cups all-purpose flour
  • 1 tsp baking soda
  • 1 tsp cream of tartar
  • 1 1/2 tsp ground cinnamon
  • 1/2 tsp ground ginger
  • 1/4 tsp ground nutmeg
  • 1/8 tsp ground cloves
  • 1/2 tsp salt
  • 1 cup unsalted butter (½ browned, ½ softened)
  • 1 cup granulated sugar
  • 1/2 cup light brown sugar, packed
  • 2 large eggs, room temperature
  • 2 tsp vanilla extract
  • as needed orange gel food coloring
  • 8 oz milk chocolate bars, chopped
  • 1/2 cup semi-sweet chocolate chips (optional)
  • to taste flaky sea salt (for topping)
  • as needed black decorating gel or melted chocolate
  • as needed orange sanding sugar (optional)
  • as needed green candy melts or frosting (for stems)

Instructions
 

  • Melt ½ cup butter in a light-colored pan until browned. Let cool to room temp. Mix with remaining ½ cup softened butter.
  • Beat butter and sugars until fluffy. Add eggs, vanilla, and orange food coloring. Mix until smooth.
  • Whisk dry ingredients separately, then combine with wet in two batches. Mix until just combined. Chill dough 30 minutes.
  • Chop chocolate bars into ½-inch chunks. Mix with optional chocolate chips if desired.
  • Preheat oven to 350°F. Scoop dough, flatten, place chocolate chunks inside, and wrap dough around to seal. Roll into balls and slightly flatten. Sprinkle with sanding sugar if using.
  • Bake 11–13 minutes until edges are set but centers still soft. Cool on sheet for 5 mins, then transfer to rack.
  • Once cool, pipe jack-o-lantern faces with black gel or melted chocolate. Add green stems with frosting or candy melts if desired. Let decorations set before stacking or storing.

Notes

Chill your dough before baking to prevent spreading. Don’t skip the brown butter step — it adds rich, nutty flavor. For best jack-o-lantern designs, let cookies cool completely before decorating. These store well and taste just as good days later. Freeze unbaked dough balls for easy prep later.

Nutrition

Calories: 210kcalCarbohydrates: 26gProtein: 2gFat: 11gSaturated Fat: 7gPolyunsaturated Fat: 0.5gMonounsaturated Fat: 2gCholesterol: 30mgSodium: 110mgPotassium: 65mgFiber: 1gSugar: 16gVitamin A: 320IUCalcium: 20mgIron: 1mg
Keyword halloween cookies, jack-o-lantern cookies, milk chocolate center, pumpkin spice cookies, stuffed cookies
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