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Rum Raisin Cinnamon Swirl Challah

Cinnamon Raisin Swirl Challah

This is the kind of challah that feels almost like a dessert,  particularly because of the cinnamon swirl inside – truly something  special to celebrate Rosh Hashanah.

I love coming up with crazy challah flavors to delight and surprise my friends and family throughout the year.

But sometimes you want something classic: plain challah with sesame seeds on top, sweet challah studded with chocolate chips, or a perfect cinnamon-raisin challah.

As we prepare to welcome Rosh Hashanah with sweet foods and prayers for the New Year, I wanted to take a classic sweet raisin challah and add in a signature cinnamon swirl stuffing for something that is a little traditional and a little wacky and fun. A bit like me. 

  • Duration
  • Cook Time
  • Prep Time
  • 2 round challotServings


  • 1 cup raisins
  • ½ cup warm water
  • ½ cup dark rum
  • 1 ½ tablespoons active dry yeast
  • 1 teaspoon sugar
  • 1 ¼ cups lukewarm water
  • 4 ½ cups unbleached all-purpose flour
  • ½ tablespoon salt
  • ½ tablespoon cinnamon
  • ¼ teaspoon nutmeg
  • ½ cup plus 2 tablespoons sugar
  • ½ cup vegetable oil
  • 1 teaspoon vanilla
  • 2 eggs
  • ½ cup (1 stick) margarine, at room temperature
  • ½ cup packed brown sugar
  • 2 teaspoons cinnamon
  • Pinch of salt
  • 1 egg + 1 teaspoon water + 1 teaspoon honey
  • Thick sea salt (optional)


1. The night before or 2 hours before you are  ready to bake your challah, place raisins, warm water, and rum into a bowl. Allow to sit while raisins absorb liquid and plump. When ready to make the dough, drain raisins and set aside.

2. In a small bowl, place yeast, 1 teaspoon sugar, and lukewarm water. Allow to sit  around 10 minutes, until it becomes foamy on top.

3. In a large bowl or stand mixer fitted with the whisk attachment, mix together 1½ cups  flour, salt, sugar, cinnamon, and nutmeg. After the water-yeast mixture has become foamy, add to flour mixture along with oil and vanilla. Mix thoroughly.

4. Add another cup of flour and eggs and mix until smooth. Switch to the dough hook attachment if you are using a stand mixer.

5. Add another 1-1½ cups flour, mixing thoroughly, and then remove from bowl and place on a floured surface. Knead remaining  flour into dough, continuing to knead for around 5 minutes.

6. Place dough in a greased bowl and cover with a damp towel. Allow to rise 3-4 hours,  punching down at least once if possible.

7. In another small bowl, mix together softened margarine, brown sugar, 2 teaspoons  cinnamon, and pinch of salt.

8. Divide dough evenly in half and then roll  each portion out into a rectangle around  ½-inch thick. Spread brown sugar mixture in an even layer all over dough, leaving a ½ inch  border all the way around. Sprinkle reserved raisins over the brown sugar mixture.

9. Working quickly, start rolling up the dough towards you. Try to keep the roll relatively tight as you go. Pinch the ends and tuck  under when you finish.

10. Create a pinwheel-shaped challah by snaking the dough around and around in a circle around itself. When finished, tuck the  end under the challah neatly and pinch lightly.  This doesn't have to be perfect.

11. Preheat oven to 350°F.

12. Allow challah to rise another 30-60 minutes, or until you can see the size has grown  and challah seems light.

13. In a small bowl, beat 1 egg with 1 teaspoon honey, and 1 teaspoon water. Brush egg wash liberally over challah. Sprinkle with thick sea  salt if desired.

14. Bake challah around 24-26 minutes or until golden brown and the middle of the challah  no longer seems gooey.

Article published in JOY of KOSHER with Jamie Geller Fall 2015. Subscribe Now.

Fall 2015 Magazine

Fall 2015 Magazine