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Chocolate Stuffed Jack-O’-Lantern Spice Cookies

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As the leaves turn brilliant shades of orange and the air becomes crisper with each passing day, the enchantment of autumn fills our hearts and homes. Say hello to Chocolate Stuffed Jack-O’-Lantern Spice Cookies, a whimsical treat that combines the flavors of fall with a surprising twist of chocolatey indulgence. These charming pumpkin shaped cookies not only embody the rustic warmth of Fall but also conceal a hidden treasure of rich, gooey chocolate, making them a perfect addition to your autumn gatherings and Halloween celebrations. So, gather your ingredients, dust off your baking skills, and let’s dive into the world of these delectable cookies that are sure to light up your taste buds and bring a touch of spooky sweetness to your kitchen.

chocolate cookies

WHAT SPICES ARE GREAT FOR COOKIES

When it comes to crafting the perfect fall-inspired cookies, spices play a pivotal role in infusing warmth and depth into every bite. The earthy allure of cinnamon, with its comforting aroma, sets the stage for the season’s festivities. Nutmeg lends a gentle, nutty undertone, while ginger adds a zesty kick that complements the sweet notes of chocolate. Together, these spices create a symphony of autumnal flavors, turning each bite of our Chocolate Stuffed Jack-O’-Lantern Cookies into a sensory journey through the cozy, spice-filled landscapes of fall. So, don’t be shy with your spice rack; let it be your guide to creating cookies that capture the very essence of the season.

MORE FALL RECIPES

Pumpkin Crumb Cake Muffins

Maple Chocolate Pecan Pie Bars

Maple Nut Cookies

Mini Pecan Pie Cookies

chocolate stuffed cookies

For full information on ingredients and quantities, please see the recipe card below.

chocolate pumpkin cookies

1. Cream the butter, brown sugar and vanilla in a stand mixer until light and fluffy (about 2-3 minutes). Scrape the sides of the bowl to make sure all ingredients are blended.

2. Add in the egg and beat until combined.

3. Add in flour, baking soda, ginger, nutmeg, cinnamon and salt. Stir until all combined and the dough forms a ball.

Pumpkin Sandwich Cookie Steps

4. Flour your work surface and roll out the dough to 1/4 inch thickness.

Cut out cookies using a pumpkin cookie cutter and carefully transfer them to a parchment lined baking sheet or use a silicone baking mat on the sheet.

pumpkin cookie cutters

Using a paring knife, cut out eyes and a mouth on HALF of the cookies – these will be the tops. Leave the other half of the cookies whole – these will be the bottoms. Place the cookies in the freezer for 15 minutes and freeze until firm.

pumpkin cookies on tray

5. Preheat oven to 350 degrees. Bake the frozen cookies for 8-10 minutes and just golden brown. Remove from oven and cool on baking pan for 10 minutes and then transfer to a cooling rack and cool completely.

6. Add the 1 TBSP of butter to a small saucepan and melt until slightly brown – takes about 2-3 minutes. Remove from heat and let cool for 5 minutes. Brush butter over the top half of the cookies with the eyes and mouths cut out. Sprinkle with cinnamon sugar.

pumpkin cookies on cooling rack

7. COOKIE ASSEMBLY: Carefully spread the melted dark chocolate over the bottom half of the cookies (the cookies with no eyes or mouth!). Place the top cookies (pumpkin face) over the chocolate and gently press down. This should create about 12 sandwich cookies depending on the size of your cookie cutter.

Cookies can be served immediately with the melted chocolate or you can wait until the chocolate firms up to enjoy. Putting them in the refrigerator to cool the chocolate completely is another great way to enjoy these cookies.

pumpkin sandwich cookies
Jack o lantern Cookies
jack o lantern cookies

Chocolate Stuffed Jack-O’-Lantern Spice Cookies

Hollie Schultz
Delicious dark chocolate sandwiched between spice cookies that create an amazing Fall cookie sandwich.
No ratings yet
Prep Time 20 minutes
Cook Time 10 minutes
Assembly 20 minutes
Total Time 50 minutes
Course Dessert
Cuisine American
Servings 12 cookies
Calories 294 kcal

Ingredients
  

  • 1/2 cup butter softened
  • 2/3 cup brown sugar
  • 1/2 tbsp vanilla
  • 1 egg
  • 1/2 tsp cinnamon
  • 1/4 tsp ginger
  • 1/4 tsp nutmeg
  • 1/4 tsp salt
  • 2 1/4 cups flour
  • 1 cup dark chocolate

Instructions
 

  • Cream the butter, brown sugar and vanilla in a stand mixer until light and fluffy (about 2-3 minutes). Scrape the sides of the bowl to make sure all ingredients are blended.
  • Add in the egg and beat until combined.
  • Add in flour, baking soda, ginger, nutmeg, cinnamon and salt. Stir until all combined and the dough forms a ball.
  • Flour your work surface and roll out the dough to 1/4 inch thickness. Cut out cookies using a pumpkin cookie cutter and carefully transfer them to a parchment lined baking sheet or use a silicone baking mat on the sheet. Using a paring knife, cut out eyes and a mouth on HALF of the cookies – these will be the tops. Leave the other half of the cookies whole – these will be the bottoms. Place the cookies in the freezer for 15 minutes and freeze until firm.
  • Preheat oven to 350 degrees. Bake the frozen cookies for 8-10 minutes and just golden brown. Remove from oven and cool on baking pan for 10 minutes and then transfer to a cooling rack and cool completely.
  • Add the 1 TBSP of butter to a small saucepan and melt until slightly brown – takes about 2-3 minutes. Remove from heat and let cool for 5 minutes. Brush butter over the top half of the cookies with the eyes and mouths cut out. Sprinkle with cinnamon sugar.
  • COOKIE ASSEMBLY: Carefully spread the melted dark chocolate over the bottom half of the cookies (the cookies with no eyes or mouth!). Place the top cookies (pumpkin face) over the chocolate and gently press down. This should create about 12 sandwich cookies depending on the size of your cookie cutter.
    Cookies can be served immediately with the melted chocolate or you can wait until the chocolate firms up to enjoy. Putting them in the refrigerator to cool the chocolate completely is another great way to enjoy these cookies.

Nutrition

Calories: 294kcalCarbohydrates: 37gProtein: 4gFat: 14gSaturated Fat: 9gPolyunsaturated Fat: 1gMonounsaturated Fat: 4gTrans Fat: 0.3gCholesterol: 34mgSodium: 62mgPotassium: 154mgFiber: 2gSugar: 16gVitamin A: 262IUVitamin C: 0.01mgCalcium: 30mgIron: 3mg
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