Chocolate Stuffed Cinnamon Sugar Jack-O’-Lantern Cookies

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Chocolate stuffed cinnamon sugar jack-o’-lantern cookies just in time for Halloween! I am amazed by how good these cookies are. They creamy chocolate layer sandwiched between two crunchy cinnamon sugar cookies is just the perfect pairing. If you’re looking for a fun fall cookie recipe, give this recipe a try!

This recipe was inspired by Half Baked Harvest’s milk chocolate stuffed jack-o’-lantern cookies! I wanted to make an allergy friendly version of her cookies, and I am so glad that I did! This is my new favorite fall cookie recipe.

Where can I find pumpkin cookie cutters?

I found these pumpkin cookie cutters on Amazon and I love them! They’re just a couple dollars and work so well. I used the smaller size (3 inch) pumpkin cookie cutter for these cookies! To make the pumpkin cookies jack-o’-lanterns, simply cut out eyes and a smile using a sharp paring knife.

chocolate stuffed jack-o'-lantern cookies close up
What ingredients will I need to make these jack-o’-lantern cookies?

Hopefully you have everything you need on hand! Here’s what you’ll need:

  • oat flour (I use homemade)
  • baking soda
  • cinnamon
  • salt
  • granulated sweetener (e.g. coconut sugar, maple sugar, date sugar)
  • vegan butter or coconut oil
  • pure vanilla extract
  • pure maple syrup (or honey)
  • chocolate chips (I use dairy free)
Help, I don’t have oat flour!

If you don’t have oat flour on hand, you can easily make your own at home. Simply blend rolled or old fashioned oats in a high speed blender until they turn into a flour. You can view a video of how I make homemade oat flour here!

chocolate stuffed jack-o'-lantern cookies on a plate
What kind of granulated sweetener should I use in this recipe?

You can use whatever kind of granulated sweetener you prefer! I used maple sugar, but coconut sugar and date sugar should also work!

Can I use honey instead of maple syrup?

I haven’t tried this recipe using honey instead of pure maple syrup, but it should work!

Do I have to use vegan butter?

If you don’t want to use vegan butter, feel free to use regular butter or coconut oil instead. I haven’t tried this recipe with either of those substitutions, but they should work just fine!

chocolate stuffed jack-o'-lantern cookies held in hand
How do I store these cookies?

I like to store these cookies in a sealed container on the counter for 4-5 days or in the freezer for long term storage!

Looking for more cookie recipes?

Try some of my other delicious cookie recipes!

Ready to make these delicious chocolate stuffed cinnamon sugar jack-o’-lantern cookies? Get the full recipe below!

Chocolate Stuffed Cinnamon Sugar Jack-O’-Lantern Cookies

Servings 10
Prep Time 50 minutes
Cook Time 7 minutes
Total Time 1 hour


For the Cookies

  • 2 1/2 cups oat flour (I used homemade)
  • 1 tsp baking soda
  • 1 tsp cinnamon
  • 1/2 tsp salt
  • 1/4 cup + 2 tbsp pure maple syrup
  • 1/4 cup + 2 tbsp vegan butter, melted (or coconut oil)
  • 1 tsp pure vanilla extract
  • 3 oz chocolate chips (I used dairy free)

For the Cinnamon Sugar Topping

  • 1 tbsp vegan butter, melted (or coconut oil)
  • 2 tbsp granulated sweetener (coconut sugar, maple sugar, date sugar, etc.)
  • 1 tsp cinnamon


  • Preheat the oven to 350°F and line a large baking sheet with parchment paper.
  • While the oven heats up, add the oat flour, baking soda, salt and cinnamon to a large mixing bowl and mix until well combined. Once combined, add in the melted butter, maple syrup, and vanilla extract and mix until a thick dough forms.
  • Place a piece of parchment paper on the counter and add the dough to the parchment paper. Gently roll out the dough using a rolling pin (if you don’t have a rolling pin, a water bottle often works instead). If the dough is sticking to the rolling pin, place a piece of parchment paper over the dough and roll over the parchment paper instead of directly on the dough.
  • Cut out the cookies using a pumpkin shaped cookie cutter. Then cut out eyes and a smile on half of the cookies using a sharp knife. Carefully transfer the cookies to the lined baking sheet.
  • Roll out any remaining dough scraps and repeat step 4 until all of the dough is used up (this recipe makes about 20 pumpkin cookies).
  • Bake the cookies in the oven for 7-8 minutes. After baking, transfer the cookies to a cooling rack to cool.
  • While the cookies cool, add the chocolate chips to a glass dish and heat them in the microwave, stirring frequently so the chocolate doesn’t burn. Set aside.
  • Combine the cinnamon and sugar in a small dish to create a cinnamon sugar mixture. Brush the additional melted butter over the top of the pumpkin cookies with faces and sprinkle the cinnamon sugar over the cookies.
  • Next spread the melted chocolate over the pumpkin cookies without faces. Then place a pumpkin cookie with a face on each pumpkin cookie without a face and gently press down into the chocolate. You can enjoy the cookies immediately or let the chocolate harden first (if you want the chocolate to harden quickly, place the cookies in the fridge for 15 minutes).



  • If the dough is too dry and falling apart, add some more melted vegan butter or maple syrup to the dough before rolling it out.
  • You should be able to use coconut oil instead of vegan butter. I haven’t tried in this recipe, but it should work!
Course: Dessert
Diet: Gluten Free, Refined Sugar Free, Nut Free, Dairy Free, Soy Free, Vegan
Keyword: Chocolate Stuffed, Cinnamon Sugar Cookies, Halloween Cookies, Halloween Dessert, Jack-O’-Lantern Cookies

Join the Conversation

  1. Steffanie Durband says:

    Hi, this recipe looks delicious and healthy and I’d love to make these for my grandkids. I tried multiple ways of saving this to my Pinterest board but it tells my there’s not a image available. Not sure if that’s something you can fix on your side. Just letting you know. For now, I’ll just copy the recipe down. I’m sure they’ll be wonderful. Thank you for all your wonderful, healthy and yummy recipes!

    1. Hi! Thanks so much for letting me know about the Pinterest issue. I’ll look into it and let you know when it is resolved! I really hope you enjoy this recipe, and I hope the grandkids do as well! 🙂

    2. I spoke with Pinterest and they said it is an issue on their end and should be resolved in a couple of days!

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