Recipe courtesy of Amy Kritzer Becker

Cinnamon Roll Challah

  • Level: Intermediate
  • Yield: 1 loaf
  • Total: 4 hr 35 min (includes standing, rising and cooling times)
  • Active: 50 min
Round challah is traditional for the Jewish New Year of Rosh Hashanah to symbolize the circle of life. This version is filled with gooey cinnamon roll spread and braided around a ramekin filled with a honey glaze dip. It makes a great centerpiece and is a tasty way to bring in a sweet New Year!
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Ingredients

Dough:

1 packet (2 1/4 teaspoons) active dry yeast

1/2 cup granulated sugar

1/4 cup vegetable oil, plus more for greasing bowl

1/4 cup honey (see Cook's Note)

3 large eggs plus 1 yolk

1 1/2 teaspoons kosher salt

4 1/2 to 5 1/2 cups bread flour

Filling:

1/3 cup canola oil, plus more for greasing ramekin

1 cup packed brown sugar

1 tablespoon ground cinnamon

1/8 teaspoon kosher salt

Honey Glaze Dip:

2 tablespoons honey

1/2 cup confectioners' sugar

1 to 2 tablespoons almond milk

2 tablespoons pomegranate arils, for garnish

Directions

  1. For the dough: Mix the yeast with 1 tablespoon of the granulated sugar in a large bowl or the bowl of a stand mixer and add 3/4 cup warm water (about 100 degrees F) to activate. Let stand until the yeast bubbles up, about 10 minutes. If it doesn’t bubble up, your yeast is not active or the water is the wrong temperature; try again with new yeast and water.
  2. Whisk the vegetable oil, honey, 3 whole eggs and remaining granulated sugar into the yeast mixture until incorporated. Then add the salt and about half the flour and mix into a ball with a wooden spoon or dough hook. Knead until smooth, about 10 minutes, adding in more flour as needed until your dough is smooth, soft and tacky but not sticky. You may not need all the flour; do not add too much.
  3. Grease a bowl and add the dough. (I clean out my mixing bowl.) Cover and put in a warm place until doubled in size, about 2 hours.
  4. For the filling: Whisk together the canola oil, brown sugar, cinnamon and salt in a medium bowl.
  5. Divide the dough into 3 equal pieces and set 2 aside. Roll out 1 piece into a 1/4-inch-thick rectangle, about 13 by 18 inches. If your dough keeps bouncing back, let it rest a moment for the gluten to relax. If it’s sticky, sprinkle with a small amount of flour. Evenly spread with a thin layer of about a third of the filling, leaving a 1/2-inch border around the rectangle. Roll it up jelly roll style, starting from the long side to get a long strand. Repeat with the other dough pieces and filling. Braid the dough pieces into a 3-strand challah.
  6. Lightly grease the outside of an 8-ounce (or smaller) ramekin and place on a parchment paper-lined baking sheet. Wrap the challah braid around the ramekin on the baking sheet and secure the ends together. Cover and let rise until the challah is light and fluffy looking, another 45 to 60 minutes.
  7. Position a rack in the center of the oven and preheat the oven to 350 degrees F.
  8. Whisk the remaining egg yolk with 1 1/2 teaspoons water in a small bowl and brush generously all over the challah. Bake until golden brown, about 35 minutes. Let the challah cool slightly.
  9. For the honey glaze dip: While your challah is baking, mix together the honey and confectioners' sugar with just enough almond milk to get a thick dip that can coat the back of a spoon.
  10. Add the dip to the ramekin, sprinkle the challah with the pomegranate arils and serve!

Cook’s Note

A tip for measuring honey: If you measure the oil before the honey using the same measuring cup, the honey will slip right out!

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