Chocolate Stuffed Gingerbread

Soft gingerbread cookies stuffed with a dark chocolate fudge. Gluten free and vegan.

soft gingerbread chocolate stuffed gingerbread vegan gingerbread gluten free gingerbread

Isn’t holiday baking just wonderful?!  The house brimming with sweet and spicy scents. Poring over Christmas lists to decide which cookie to send to which friend. Licking the fringes of dough from the mixing spoon.

These cookies were inspired by the carol of The Friendly Beasts. It’s the start of a four-part mini series, each recipe  dedicated to a different beast in the song. There is a Tomie DePaula book based on the carol. My mother says I recited the book for my family when I was little, but I have no such memory. The tune has its roots in 13th century France, and has many versions — English and French and Latin and German. My favorite is the one by Sufjan Stevens.

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“I”, said the donkey, shaggy and brown/ “I carried His mother uphill and down/ I carried her safely to Bethlehem town/ I” said the donkey, shaggy and brown.

I’ve called these cookies “shaggybrowns” after that donkey. They are a bit raggedy and coarse in appearance, but are hearty and spicy and comforting. And who doesn’t enjoy chocolate-stuffed cookies? My little 8 year old niece loved them, and my she’ll-kill-me-if-I-tell-you-how-old-she-is mother loved them, and everyone in between did too.

soft gingerbread cookies chocolate stuffed gingerbread gluten free gingerbread vegan gingerbread

The cookie base is a little less sweet and spicy than traditional gingerbread. I didn’t want the sweetness or pungency of the cookie overwhelm the wonderful fudge filling. This version has no ground cloves or allspice, and less molasses than usual. I also swapped out the butter for unsweetened applesauce. The dough will be rather sticky but still manageable. Just make sure you chill the dough and dust it before rolling.

They bake up all puffy and chewy. They stay chubby as they cool, which makes it easy to slice and stuff them. As I mentioned in some earlier posts, I’ve recently taken to a lazy-but-efficient way of melting chocolate. Simply fill a thick freezer bag with chocolate +maple syrup and immerse in hot water till melted. Snip off the a corner of the bag to pipe the chocolate onto the cookies. I wouldn’t try this method with chocolate that I wanted to look shiny and tempered, but it works very well here.

I added these to the list of must-makes at holiday time, and I hope you will too.

soft gingerbread cookies chocolate stuffed gingerbread cookies gluten free gingerbread vegan gingerbread


On Thursday, I’ll be posting the next part in the series, “the cow all white and red.” Don’t worry, it’s not beef!!

Chocolate Fudge Stuffed Gingerbread

Prep Time: 30 minutes

Cook Time: 9 minutes

Yield: approx 45 cookies

I like to use Bob's Red Mill cup-to-cup GF flour (not sponsored). But I have found over many trials, that even the finest GF flour needs to be very well sifted in order to yield the best results. I like to sift at least twice. So take your time sifting, and you will be rewarded.

Oh...I forgot to tell you! This is a one-bowl kinda thing. Isn't that the best? Less dishes, hurrah!


  • 3 cups of very well sifted gluten free flour (just under 12 oz)
  • 3/4 cup packed brown sugar
  • 1/2 cup molasses
  • 1/2 cup unsweetened applesauce
  • 1 tbsp ginger
  • 1 tbsp vanilla or rum
  • 1 tsp cinnamon
  • 1 tsp salt
  • 1 tsp baking soda
  • more flour, for dusting
  • filling
  • 2 cups of chocolate chips
  • 2/3 cup maple syrup


  1. Combine brown sugar, molasses, applesauce, ginger, vanilla/rum, cinnamon, salt, and baking powder. Stir.
  2. Gradually add the flour to the molasses mix and stir till combined. Dough will be sticky.
  3. Cover dough with plastic and allow to chill for at least two hours.
  4. After dough is chilled, preheat oven to 350.
  5. Roll some parchment paper out on the counter or table, and dust it with flour.
  6. Place the dough on your prepared surface, add more flour to the top of the dough, and a second piece of parchment. Roll dough out to 1/4 inch thickness.
  7. Use a biscuit cutter (about 2.5 inches) to cut out the cookies. Re-roll and cut as needed.
  8. Place the cookies on the baking sheet. You can crowd them (they can even be touching), as they won't spread a single inch.
  9. Bake for 9 minutes, or just under. They will have puffed up wonderfully.
  10. Allow cookies to cool and then gently slice each cookie in half.
  11. Put the chocolate chips and maple syrup in a big plastic freezer bag. Let them melt, but not too drizzly. You want the chocolate to be stiff enough to pipe without melting all over the place.
  12. Pipe just under a tablespoon of chocolate onto each bottom cookie half. Top with other cookie half.
  13. Serve and enjoy! Store in an airtight container for up to a week, but are best within the first three days. These freeze very well.
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cookie base adapted + modified from Mel’s Kitchen Cafe


8 thoughts on “Chocolate Stuffed Gingerbread

  1. The holiday season was made for baking cookies and other sweet treats if you ask me! I just LOVE the wonderful smells coming from the oven wafting through the house. *swoon* These cookies look marvelous!! Soft gingerbread cookies stuffed with chocolate fudge?! What’s not to love, right?! Cheers!!

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