Whole Wheat Cinnamon Raisin Challah

Are you a cinnamon raisin lover like me? I love the toasted bagel version with a shmear of cream cheese. That was my inspiration behind creating a whole wheat cinnamon raisin challah recipe!

Why whole wheat?

The reason I chose to use whole wheat, is because I like the nuttiness that it brings to the table. If you prefer, you can substitute for white whole wheat which has a milder flavor, and is lighter in color.

How to make Challah:

It can seem a little intimidating to bake challah if you’ve never tried it before. The dough itself is simple to make and easy to work with once it’s formed. What you should be preparing yourself for, is the aroma of it baking, it’s devine!

  1. Proof the yeast. Combine the warm water, yeast, and sugar in a large bowl. The sugar is essential to the dough, as it helps produce carbon dioxide, the leaving gas which causes the dough to rise! Set this bowl aside while you mix together the remainder of the ingredients.
  2. Combine the remaining sugar, flours, cinnamon, salt, eggs, and honey in the bowl of a stand mixer fitted with the dough hook. (You can definitely also make this by hand, but do count it as your workout!)
  3. Add your yeast mixture to the bowl and knead on medium-low for 5 minutes, adding more flour as needed. Fold in the raisins.
  4. Place the dough in a greased bowl with a damp warm towel on top. Let it rise for about 1 1/2 hours, or until doubled in size.
  5. When the dough is ready, measure it into equal sized pieces and braid. Set aside to rise for an additional 45 minutes.
  6. Brush the challah with egg wash and bake on a parchment lined baking sheet for 35-45 minutes, until the top and bottom of the loaf are golden brown.

Braiding the challah:

It’s traditional to eat round Challahs on Rosh Hashanah to symbolize the cycle of the year. Feel free to braid it however you would like! Here’s how I braided my whole wheat cinnamon raisin challah:

Whole Wheat Cinnamon Raisin Challah

Whole wheat cinnamon raisin challah is the perfect way to start off your Rosh Hashanah meal.
Servings 2 large round challahs


  • 2 envelopes active dry yeast
  • 1 1/2 cups warm water
  • 1 tsp sugar
  • 1/2 cup sugar
  • 2 1/2 cups whole wheat flour or white whole wheat
  • 4 cups all-purpose flour plus more for sprinkling
  • 2 tsp ground cinnamon
  • 2 tsp salt
  • 2 large Eggs
  • 3/4 cup neutral flavored oil
  • 4 tbsp honey
  • 1/2 cup raisins


  • Combine the yeast, warm water, and 1 tsp of sugar in a bowl. Set aside to proof.
  • In a large bowl, or a stand mixer fitted with the dough hook, combine the remaining sugar, flours, cinnamon, salt, eggs, oil and honey. Mix very well.
  • Add in the yeast mixture and knead for approximately 5 minutes. Add in more flour as needed. 
  • Fold in the raisins. Place in a greased bowl with a warm wet towel on top, and set in a warm place to rise for around 1 1/2 hours.
  • When the dough has double in size, measure into equal parts (pictured is a 4 braid round loaf) and braid. Place in a greased round pan (8") or on a parchment lined baking sheet and set aside to rise for 45 minutes to an hour.
  • While the challah is rising for a second time, preheat your oven to 350 F.
  • Brush with egg wash and bake on 350 F for approximately 35-45 minutes, or until the top is dark golden brown.

Of course you can make this ahead of time. Challah freezes beautifully!

I always love to see which recipes you are making from my blog, so don’t forget to tag me @tomatoes_tomahtos! Feel free to check out more Rosh Hashanah recipes including this Rich Chocolate Pomegranate Tart and these Apple Crumble Bars.

Until next time,


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