Cinnamon Chocolate Chip Challah

First of all I want to say that my house smells amazing. Your house can smell amazing too! I made this delicious cinnamon and chocolate challah this morning and the bread perfumed my little old apartment. My dogs didn’t seem to mind the wonderful smell of baking bread either. They were both adorable and sat by the oven the whole time my challah was baking.

Now, I have to confess I have never made challah before until this week. Let me tell you, it’s super easy to make! When I was thinking earlier this week what I should make for the blog, I couldn’t forget how awesome last week’s Kanelbullar came out, so in the same cozy and hygge-filled spirit, I wanted to make homemade bread. Challah is one of those bread recipes that is not super difficult to make. In fact, a traditional challah is one of the easier yeast breads to make. So, I decided to make my challah a little different by adding… chocolate and cinnamon, of course. And because I love myself, too.


You want to combine your flour, sugar, and salt.


You will also want to activate your yeast with water and a pinch of sugar.


It is ready when it is foamy.


Make sure you whisk you all of your dry ingredients.


Just give the yeast about 10 minutes to activate.


Have your 2 whole eggs and extra egg yolk ready. In another bowl, save the egg white and set it aside for later.


Once your ingredients are ready, you can start making the dough!


Make a well in the center of the flour mixture and add your eggs, yolks, and oil to the center.


Knead the dough for about 6 minutes. The dough will be a firm ball.


Put the dough in an oiled bowl and cover that bowl with plastic wrap.


Meanwhile, you can start making the filling.


Simply mix sugar, oil, cinnamon, and salt together.


Once your dough has doubled in size, you are ready to roll.


Damn Gina!!


Put the dough out on a floured surface and divide it into three even pieces.


Roll out each piece into a rough square and spread the filling on the dough, leaving some room around the edges.


Sprinkle-dinkle the chocolate chips over the filling.


Roll each square of dough up into a tube.


They will be about the same size.


You will want to roll each piece of dough into a rope of about the same size. Pinch the ends of the rope to seal the filling.


Next, you will start making the braid. You will do this like you would braid hair or yarn.


It will look roughly like this. Or better. Let the dough rise for another 30 minutes.


While you heat up the oven to 375 degrees F, you can brush the dough with the egg whites you set aside. This will start a crust on the bread.


Right before you put the dough in the oven, brush the dough with egg white again.


You can bake it for about 35 to 45 minutes or until a thermometer reads 190 on the center of the bread.


Awe, look at that cutie in the corner. Pickles is just waiting for a crumb to fall, but that’s not happening.


Cinnamon Chocolate Chip Challah

Servings: 1 loaf
Author: Melanie, Coffee ‘n Spice
Recipe Adapted from The Kitchn


2 teaspoons active dry yeast
1 cup lukewarm water (110 degrees F)
4 to 4 1/2 cups all-purpose flour
1/4 cup cane sugar (regular white sugar works too)
2 teaspoons salt
3 eggs (reserve the white of one egg for the egg wash)
1/4 cup vegetable oil or grapeseed oil
1/3 cup vegetable oil or grapeseed oil
3/4 cup brown sugar
2 teaspoons cinnamon
1 dash salt
½ cup of kosher semi-sweet chocolate chips*

*If you don’t need to keep a kosher table, you can substitute melted butter for the oil in this recipe. You can also use non-kosher chocolate chips as well.

  1. Sprinkle the yeast over the water in a small bowl (I used my liquid measuring cup, to make it easier to pour), and add a healthy pinch of sugar. Let the yeast stand until you see a thin, frothy layer across the top. This will take about 10 minutes.
  2. Whisk together sugar, salt, and 4 cups of your flour in the bowl of a standing mixer with the hook attachment, or you can mix it by hand in a bowl.
  3. Make a well in the center of the flour and add the 2 whole eggs, egg yolk, and oil. Whisk these together to form a slurry. Make sure to scrape the flour from the sides of the bowl.
  4. Next, pour the yeast mixture over the egg/flour mixture. Mix the yeast, eggs, and flour with the hook attachment of your stand mixer.
  5. Knead the dough for 5 to 6 minutes with a dough hook attachment, knead the dough on low speed. Or you can turn out the dough onto a floured work surface and knead by hand for about 10 minutes. If the dough seems very sticky, add a little more flour. Once the dough is soft, smooth, and holds a ball shape, it is ready.
  6. Let the dough rise until it has doubled. Place the dough in an oiled bowl, cover with plastic wrap, and place somewhere warm. Let the dough rise for about 90 minutes.
  7. Separate the dough into three equal pieces. Roll each one into a square with a rolling pin. Spread the cinnamon-sugar mix on the dough, leaving a 1/2 inch around the edges. Then sprinkle some of the chocolate chips over the spread. Next, roll each piece of dough into a long rope, roughly 1-inch thick and about 16 inches long. Make sure to pinch the ends of the rope as you roll to seal the filling.
  8. Next is the fun part: gather the ropes and squeeze them together at the very top to seal them together. If making a 3-strand challah, braid the ropes together like braiding hair or yarn and squeeze the ends together when complete. After you have your challah braided, you will want to line a baking sheet with parchment and put the loaf on top. Make sure to braid the dough with the seam of the rope facing down or your filling will spill out. Sprinkle the loaf with a little flour and drape it with a clean dishcloth. Place the pan somewhere warm and let it rise for about 30 minutes.
  9. Brush the challah with egg white that was set aside while you preheat your oven to 375 degrees F. When ready to bake, whisk the reserved egg white with a tablespoon of water and brush it all over the challah once more. Make sure to get in the cracks and down the sides of the loaf.
  10. Bake the challah for 35 to 40 minutes, rotating the pan halfway through cooking. The challah is done when it is deeply browned and registers 190°F in the very middle with an instant-read thermometer. Enjoy!

Print – Download – Cinnamon Chocolate Challah Bread


Well, that’s all I have for you guys today. I hope you guys enjoyed this post. Let me know what you think. If you decide to make this recipe and it turns out looking better than my challah, post a picture. Enjoy your weekend!




One thought on “Cinnamon Chocolate Chip Challah

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