Cinnamon Roll Challah (with Recipe Video)

The wonderful and comforting taste of a cinnamon roll in the form of a beautiful, braided challah loaf.

Challah (Hallah) is a traditional, braided Jewish bread. It is a staple for Shabbat and other special days. You can find many varieties of challah, from simple to enriched and flavored.

This particular version is every so lightly sweetened and has a ribbon of cinnamon throughout. I used sucanat in the bread, and brown sugar in the filling.

What is Sucanat?

Sucanat comes from natural sugar cane juice, just like typical granulated or brown sugar. However sucanat is made from extracting the sugar cane juice, boiling it, and then beating it with paddles (or done by machines) to make granules.

It does not undergo any refining processes, so it still contains traces of molasses, which gives it a characteristic brown color, and richer flavor.

Because it is much less processed than traditional sugar, it contains more vitamins and minerals.

To Make This Recipe You Will Need:

• unbleached bread flour
• eggs
• water
• butter
• powdered milk
• sucanat
• salt
• instant yeast
• brown sugar
• butter
• cinnamon
• mixing bowl with dough hook (or mixing bowl if you wish to mix and knead by hand)
• baking sheet or stone
• parchment paper
• kitchen towel (lint-free)
• whisk
• small bowl
• pastry brush
• cooling rack

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Watch Me Make this Recipe in the Video Below

To begin, combine 3 1/2 cups of the bread flour in your mixer’s bowl. Add in the sucanat, instant yeast and salt.

Add the water, egg and egg yolk, and turn your mixer on (using the dough hook attachment.)

Add in the softened butter.

While the dough is mixing, add additional bread flour in very small increments, until it reaches a nice soft consistency. This may take up to an additional 1 cup of flour, making 4 1/2 cups total. The amount will vary based on moisture and humidity.

Mix for 5-7 minutes, or until the dough is nice and elastic.

Drizzle a tablespoon of extra virgin olive oil in a large bowl.

Form the dough into a nice, smooth ball. Place the dough in the bowl, top down, sliding it around to coat, then turn it over so that the smooth side is facing up.

Cover the dough with a damp, lint-free kitchen towel (tea towel/flour sack towel) and let it rise for 1 hour in a warm location, or until it is doubled in size.

Then “punch down” the dough and give it a quick kneading to remove air bubbles.

In a small bowl, combine your filling ingredients, and whisk them together.

Divide the dough into 3 or 4 sections (depending on how you wish to braid it.)

Take one section and roll it out into a large rectangle.

Brush 1/4 or 1/3 of the cinnamon mixture. (Depending upon how many sections you made.)

Roll it up into a log, pinching the edges together. Repeat with all of the dough portions.

Slightly stretch the rolls, and then braid them together. Place the loaf on a rimmed baking sheet that is lined with parchment paper.

Cover again with the damp tea towel, and let it rise for 45-60 minutes. When it is nearly done rising, preheat your oven to 350°(F).

Coating the Loaf

Create an egg wash by whisking the remaining egg, teaspoon of water and tiny pinch of salt in a small bowl. Use a pastry brush to brush it all over the loaf, avoiding where the loaf touches the baking sheet or stone.

Bake for 30 minutes or until golden and beautiful.

Transfer the loaf to a cooling rack and allow it to cool until it is at least nearly room temperature.

One last thing… as a “food blogger” I do a lot of photography.

Every photo on this website has been taken by ME (except for the rare image that is noted as such.) That means chasing natural light, and taking photos in odd locations, like on a bucket of grains, next to a glass door.

Right in view of my most gluttonous chickens. Watching. Waiting. Glaring at me through the glass…

Remember to let this gorgeous bread fully cool before cutting into it.

If you cut into hot bread, you lose all of the moisture through steam loss, and your bread will become dry. When you do cut it, use a nice sharp serrated bread knife. I like this one.

Enjoy!

Did you Make this Recipe? I’d love for you to give me a 5 star rating in the recipe card below. If you share it on Instagram, please tag me! You can also post it to my Facebook Page.