Cinnamon Chocolate Chip Challah

Celebrate Hanukkah with this sweet Cinnamon Chocolate Chip Challah recipe.

The foods of Hanukkah are simple, yet indulgent. Fried potato latkes, fried jam-filled sufganiyot (doughnuts), rugelach cookies, and cheese blintzes are some of the most common foods eaten during the holiday. The common thread between these food traditions? They’re all made with either oil or dairy.

Significance of oil and dairy in Hanukkah Foods

Fried foods are popular during Hanukkah because they symbolize the miracle of the oil that lit the menorah for eight days after Greece invaded Israel during the Greek Seleucid Empire. Their temple in Jerusalem was left in a complete state of disorder and only a small amount of olive oil was left to light the menorah. The oil that should have lasted for only one day miraculously lasted for eight days — the number of days Hanukkah is now observed.


Shemen is the Hebrew word for oil. Coincidentally, the similarly spelled Shemoneh is the hebrew word for eight, the same number of days the oil burned.

Cinnamon Chocolate Chip Challah

During the time of the war against the Greeks, a woman named Yehudis used a dairy product as a tranquilizer for a Greek general. She fed him salty cheeses that made him very thirsty and gave him wine to quench his thirst. Eventually, the general got very drunk and passed out. Yehudis took this as an opportunity to kill him, causing chaos within the Greek army that led to them fleeing Judea. Therefore, celebrating Hanukkah with foods made of dairy is a way to honor the bravery of Yehudis.

Cinnamon Chocolate Chip Challah

While dairy isn’t a main ingredient in this Cinnamon Chocolate Chip Challah, dairy can easily be incorporated by slathering a slice of the bread with butter, or using it in french toast or bread pudding.

The Cinnamon Chocolate Chip Challah is also sweetened in part with honey, which has long held significance in the Jewish culture. During Rosh Hashanah, challah is often dipped in honey before eating.

Cinnamon Chocolate Chip Challah

Cinnamon Chocolate Chip Challah

Cinnamon Chocolate Chip ChallahCinnamon Chocolate Chip Challah
This twist on the classic Jewish challah bread combines cinnamon and chocolate for a sweet treat during Hanukkah.
Prep Time 2 hours
Cook Time 35-45 minutes
Yield 1 loaf

Ingredients
1 packet active dry yeast (3/4oz)
1/2 cup warm water
1 tablespoon honey
4 tablespoons unsalted butter, melted and cooled
1/4 cup granulated sugar
1 tablespoon cinnamon
3 eggs
1 tsp kosher salt, plus additional for sprinkling
4 cups all-purpose flour
1 cup chocolate chips

Method
Whisk yeast, warm water, and honey in the bowl of a stand mixer. Allow to proof for 5 minutes or until foamy.

Add the melted butter, sugar, cinnamon, 2 eggs, and salt, whisking to combine.

Using the dough hook attachment, slowly add the flour and then mix for 8 minutes to form a sticky dough.

Form the dough into a ball and place in a large bowl that has been greased with olive oil. Allow to rise in a warm place, such as inside your oven (turned off) for about 1 hour, until the dough has doubled in size.

Turn the dough out onto a floured surface. Divide into half and cover one half with a towel. Sprinkle half of the chocolate chips onto the dough and work them in by rolling and squeezing the dough into a 20-inch long rope, tucking chocolate chips in as you go. Repeat with the second portion of dough.

Cut the two ropes in half, so you have 4 10-inch ropes. Line them up next to each other and pinch fold the tips of the ropes together to anchor them. Cross the second rope over the third rope. Cross the fourth rope over these two and under the first rope. Cross the first rope all the way over so it now becomes the fourth one. Continue crossing the braids over one another once more, then tuck the ends underneath together and pinch to hold. Transfer to a parchment lined baking sheet.

Whisk the remaining egg and thoroughly brush over the dough, covering all crevices. You will have egg left over. Cover with a towel and put in a warm place to rise again for 30 minutes.

Preheat the oven to 350 degrees. Brush the dough once again with the remaining egg, then sprinkle with salt. Bake for 35-45 minutes, until dark brown. It is done when you knock on the bottom of the bread and hear a hollow sound.

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