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Chocolate Stuffed Pumpkin Cookies

10/29/2025

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When I think of Halloween - these are the pictures that come to my mind.🐇🦕🐕‍🦺🎃🤠 (I have no idea where the sombero cowboy costume came from.😂 )
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I have mixed feelings about Halloween.  There are parts of it that I don't love.  I hate scary movies, creepy decorations and the overabundance of sugary treats but there are things about Halloween that I do enjoy.  I loved making homemade costumes for the kids, carving jack 0'lanterns and eating roasted pumpkin seeds.🎃  
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The goal is to hand out all of the candy in our bucket to the trick or treaters on Friday so we don't have leftovers. Speaking only for myself, of course.😅   Not to worry though - I'll be making  Halloween CharBOOterie for us to snack on while we pass out treats.  What is CharBooterie, you ask?😅  Basically, Halloween themed snacks and goodies like cheese cut into cat shapes and pumpkin shaped sandwiches.🐈‍⬛🎃 🤣  

Halloween is the perfect excuse for me to break out my Jack O'Lantern cookie cutters.  I've use this cookie cutter almost every year to make sugar cookies and cut peanut butter and grilled cheese sandwiches.  This year I used it to make Chocolate Stuffed Pumpkin Cookies.  The lightly spiced dough is the perfect base for the dark chocolate center and browned butter and cinnamon sugar topping.  They're amazing and if you happen to knock on my door on Halloween night - I just might put one in your hand too.  
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Chocolate Stuffed Pumpkin Cookies
1 1/2 cups butter, softened
1 1/4 cups light brown sugar, packed
1 Tablespoon vanilla
2 eggs, room temperature
4 1/2 cups flour
1 teaspoon baking soda
1 teaspoon cinnamon
1/2 teaspoon ginger
1/4 teaspoon nutmeg
1/2 teaspoon salt
12 ounces chocolate, melted

Cinnamon Sugar Topping

2 Tablespoons butter
3 Tablespoons cinnamon sugar
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Cream together the butter, sugar, and vanilla until light and fluffy.  
Beat in eggs one at a time.  
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Add flour, baking soda, cinnamon, ginger, nutmeg, and salt.  
Divide the dough in half and flatten each half into a disk.
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Roll out the dough to 1/4 inch thickness. ​
Cut out the cookies using a pumpkin cookie cutter.  Cut face using knife.
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Place on silpat lined baking sheet and freeze 20 minutes.  
Bake 8-10 minutes at 350.
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Brown butter in skillet.  
Brush butter over half of cookies.
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Sprinkle with cinnamon sugar.  
Add melted chocolate to half of cookies. 
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Top each chocolate cookie with a cinnamon sugar cookie.
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Ciao!
Click here for a printable version of this recipe
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