Chocolate Cranberry Challah Rolls with Citrus Sugar

Simple, sophisticated and just a little fancy.

It’s almost Rosh Hashanah and so by my clock, time for another sweet challah recipe for the New Year. And one of the easiest ways to make a sweet, crowd-pleasing challah is to add chocolate chips of course.

Chocolate chip challah on its own is delicious and doesn’t need much other than a little vanilla and cinnamon. But it’s also great when you make double chocolate challah with a chocolate dough or peanut butter and crumb topping. But this High Holiday season I wanted something that was simple, sophisticated and maybe just a little fancy all at the same time.

cranberry chocolate challah rolls vertical

If you’ve never made challah rolls, they are so easy. In fact sometimes I find them even easier than braiding a regular challah. I suggest using a kitchen scale to measure 2.5-3 oz pieces so the rolls are as uniform as possible. By measuring your rolls, you also ensure they will also bake evenly. Here is how I make mine:

how to make challah rolls1

If citrus isn’t your thing just top with a sprinkle of thick sea salt or substitute with a cinnamon sugar topping. This can also be made with dried cherries instead of cranberries, another favorite combination.

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For the challah:

1 ¼ cups lukewarm water

1 ½ Tbsp dry yeast

1 tsp sugar

41/2 -5 cups all purpose unbleached flour

½ Tbsp salt

¼ cup vegetable oil

½ cup sugar

1 tsp vanilla

1 tsp cinnamon

¼ tsp nutmeg

2 eggs

½ cup dark or semi sweet chocolate chips

½ cup dried cranberries

For the topping:

2 egg yolks + 1 tsp water

½ cup sanding sugar

½ Tbsp orange zest


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

In a large bowl or stand mixer fitted with the whisk attachment, mix together 1 ½ cups flour, salt, sugar, vanilla, cinnamon and nutmeg. After the water-yeast mixture has become foamy, add to flour mixture along with oil. Mix thoroughly.

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

Add another 1-1 ½ cups of flour, mixing thoroughly and then remove from bowl and place on a floured surface. Knead remaining ½ cup flour into dough, continuing to knead for around 5 minutes. Try not to add too much flour – the less flour you add, the lighter the challah.

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

Preheat oven to 350 degrees.

Combine ½ cup sanding sugar and ½ Tbsp fresh orange zest in a small bowl. Set aside.

Braid challah into desired shape. Allow challah to rise another 45-60 minutes, or until you can see the size has grown and challah seems light.

In a small bowl beat 2 egg yolks with 1 tsp water.

Brush egg wash liberally over challah.  Sprinkle citrus sugar on top.

If making one large challah, bake around 28-30 minutes; if making two smaller challahs, bake 24-26 minutes.  If making rolls, bake 20-22 minutes or until golden on top.

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