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Cinnamon Raisin Round Challah Bread

Cinnamon Raisin Round Challah bread is light airy and soft. Each strand is filled with warm cinnamon-sugar and sweet raisins. A special bread baking project that is worth all the effort!
Prep Time2 hrs
Cook Time45 mins
Course: Bread
Cuisine: American
Keyword: challah, Jewish bread, yeast dough
Servings: 2 round loaves
Author: Lora


  • 1 package 2 1/4 teaspoons active dry yeast
  • 1 cup warm water no more than 110°F [43°C]
  • 1/3 cup sugar
  • 4 1/2 to 5 cups bread flour (about 680 grams) or 5 1/2 to 6 cups (about 750 grams) bleached all-purpose flour
  • 3 eggs
  • 1/4 cup peanut corn, or canola oil
  • 2 teaspoons salt
  • 1 Tbsp. ground cinnamon
  • 1/4 cup white granulated sugar
  • 1/2 to 1 cup raisins according to taste
  • 4 Tbsp melted butter
  • 1 egg
  • 1 teaspoon sugar


  • In a mixer, with a dough hook attachment, add the warm water and yeast.
  • Mix until blended. Add the sugar and mix about a minute.
  • Slowly mix in 1 cup of the flour until combined. Mix in the eggs one at a time until they are combined. Add another 2 cups of the flour, oil, and salt.
  • Mix together on medium-low speed stopping the machine to scrape down the sides of the bowl.
  • Slowly add the rest of the flour (the remaining 3 cups) and mix until combined. If using AP flour it's about 6 cups (about 750 grams) of flour. If you use bread flour, it's about 5 cups (about 680 grams) of flour. Stop the machine as you add each cup of the flour to scrape the sides of the bowl and incorporate the flour.
  • Mix on low speed for 12 minutes until dough is incorporated. Be sure to give your mixer a break and as you don’t want to burn it out. Add flour if needed 1 tablespoon at a time. The dough will be a little sticky but also firm.
  • Take dough out of mixer bowl. Form the dough into a ball and place into an oiled bowl (when I put the dough in the bowl and I swish the dough around the bottom of the bowl and then flip it over so all of the dough is covered in a light film of oil. I use vegetable oil).
  • Cover with plastic wrap and let it rise at room temperature until doubled in size (about1-1 1/2 hours).
  • Punch down the dough. Divide the dough into 6 equal portions.
  • Shape each portion into a ball, and allow it to rest with plastic wrap on it for 5-10 minutes.
  • Cover 3 of the dough balls and let them rest. Roll 3 of the dough balls into long piece and then flatten to form a rectangle. Brush the top with melted butter and sprinkle with the cinnamon sugar filling.
  • Top with raisins.Pinch together to form 3 filled strands.
  • Carefully move the 3 filled strands onto a sheet of parchment paper.
  • Braid the strands together to form a loaf. Carefully twist the braid around into a round loaf.
  • Rip the parchment paper around the sides of the loaf and leave a little to be able to lift the bread up. Lift up the loaf, and place into a spring form pan that has been sprayed with baking spray.
  • Repeat process with the other 3 dough balls.
  • Cover and let rise in a draft free place for about 30 minutes (I let mine rise for just about 15).
  • While resting, preheat oven to 350 F.
  • When ready to bake, brush with egg wash.
  • If making one large loaf, bake the challah for 30 minutes (on 350 F).
  • Lower the heat to 325 F and bake for about another 25-30 minutes.
  • If making two round loaves, the bread may be done in about 45 minutes.
  • You still could lower the heat after the first 30 minutes.
  • The bread should be golden brown.
  • Ovens may vary so check your challah see how it’s doing. If the top is browning too much, cover with foil for remainder of baking time.
  • Let it cool and serve slightly warm or at room temperature.