cinnamon roll challah recipe •

Cinnamon Roll Challah Bread Recipe

Cinnamon Roll Challah Bread is a perfect treat for the holidays!
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Prep Time 40 mins
Cook Time 30 mins
Total Time 1 hr 10 mins
Course Bread, Breakfast
Cuisine American, Holiday


for the challah

  • 2 1/4 teaspoons 1 packet active dry yeast
  • 3 tablespoons plus 1 teaspoon honey
  • 1 tablespoon molasses*
  • 2/3 cup warm water
  • 1/3 cup olive oil, plus more for the bowl
  • 2 large eggs
  • 1 teaspoon sea salt
  • 4 cups all-purpose flour

for the filling

  • 1/2 cup brown sugar
  • 2 tablespoons granuated sugar
  • 1 teaspoon ground cinnamon
  • 1 teaspoon ground ginger*
  • 1/4 cup butter, melted
  • 1/4 teaspoon salt
  • 1 tablespoon molasses*

for the egg wash

  • 1 large egg
  • 1 tablespoon coarse sugar


for the dough

  • Whisk the yeast and 1 teaspoon of honey with the warm water (you can do this in a stand mister or in a large bowl if you're making the bread by hand). Let the yeast stand for a few minutes to proof it until you see that it is foamy (aka alive and working). 
  • Mix in the remaining honey, molasses, olive oil and eggs. With the dough hook attachment or with a wooden spoon (if you're mixing by hand) slowly add in the salt and flour and mix until the dough forms a ball. Knead for 5 to 8 minutes (by hand or with the stand mixer dough hook). 
  • Transfer the dough to an olive-oil coated bowl, cover with plastic wrap, and let rise for 1 hour or until almost doubled in size.

for the filling

  • Melt butter then add in the sugars, spices, salt,and molasses. Set aside

forming and braiding the challah

  • Divide the dough into three even balls. Set two aside and roll out the first into a large round circle (10-12 inch diameter). This doesn't have to be perfect. Spread out 1/3 of the ginger/cinnamon filling onto the circle and then roll the circle into a long, tight rope, trapping the filling within. Gently stretch the rope by squeezing it and holding it vertically, letting its own weight stretch it. Repeat with remaining two dough balls.
  • On a parchment covered baking sheet, lay out all three long ropes side by side. Pinch together all three ropes at one end. Then braid the ropes just as you would normally braid anything. Once you're at the end of the ropes, fold the end under and pinch to seal. If you'd like to make a wreath or round braided bread, then you can pinch the two ends together (pictured above).
  • Brush with egg wash (and set the egg wash aside for another brushing later) then let rise for another hour.
  • Preheat oven to 375 degrees. Brush the challah braid again with the egg wash and then sprinkle with coarse sugar.
  • Bake for 30-35 minutes (center of the loaf should be 195 degrees). If the dough starts to get too brown cover with foil for the last few minutes.


You can use honey instead of molasses if you don't have molasses on hand. Also, I prefer a ginger-y cinnamon roll but if you want it heavier on the cinnamon side, just cut the ginger measurement in half.
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