chocolate challah
One large loaf or two smaller loaves

Double Chocolate Chip Challah

What's better than challah? Chocolate chip challah laced with chocolate chips, cinnamon, vanilla and dark cocoa powder.

I always say that I loathe Passover, but there is a part of me that also enjoys it. Or at the very least, appreciates its value. It’s a week where we are challenged to be even more thoughtful about the food we eat and where it comes from. And it’s almost like our own version of a Spring cleanse. Bye-bye carbs, hello vegetables and creative use of potatoes. I do feel lighter after a week without bread and pasta, despite my bitching and moaning all the way through. And believe me, my husband can vouch for my constant kvetching.

But the time has come to indulge in some carbs once again, and I can’t wait to get back to my Friday routine of baking challah with my daughter.

And do you know what’s better than challah? Chocolate chip challah. And perhaps even better than chocolate chip challah? Double chocolate chip challah laced with cinnamon, vanilla and dark cocoa powder.

I swear by Hershey’s Special Dark cocoa powder and highly recommend you keep it stocked for cookies, cakes and sometimes even challah.



1 1/2 Tbsp active dry yeast

1 1/4 cup lukewarm water

1 tsp sugar

5 cups all-purpose unbleached flour

3/4 cup sugar

1/2 Tbsp salt

2 tsp cinnamon

2 tsp vanilla

1/4 cup vegetable oil

2 large eggs

1/3 cup Hershey’s Special Dark Cocoa Powder

1 cup semi-sweet chocolate chips, divided

1 egg yolk

thick sea salt (optional)


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 whisk attachment, mix together 1 1/2 cups flour, salt, sugar, vanilla, cinnamon and vegetable oil. After the water-yeast mixture has become foamy, add to flour mixture. Mix thoroughly.

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

Remove approximately half the dough and place in a large bowl. Add cocoa powder and 1/2 cup flour and mix. Add half the chocolate chips another 1/2 cup-1 cup of flour and knead on a lightly floured surface until dough is smooth and elastic. Add more floured if needed. Set aside.

Add the remaining chocolate chips and 1/2 -1 cup flour to the plain dough and mix into dough. Add another 1/2 cup flour and continue knead on a lightly floured surface for around 10 minutes or until the plain dough is also elastic and smooth. Add more flour if needed.

Place both doughs in separate greased bowls and cover with damp towel. Allow to rise 3-4 hours.

Preheat the oven to 350 degrees.

Combining dough from both the plain and chocolate challah, braid into one large loaf or two smaller loaves. If attempting a six braid, I like this video tutorial.

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

Beat 1 egg yolk and brush liberally over challah. Sprinkle thick sea salt on top if desired.

Bake for 27-30 minutes, or until middle looks like it has just set, and the color is golden.

Keep on Noshing

Peanut Butter Chocolate Chip Challah

Challah is sort of my thing. I’ve been baking my own and tweaking my recipe since I am 16 years ...

Berry-Stuffed Challah French Toast

Having leftover challah has never been a bad thing. Sunday morning brunches, Shabbat afternoon sandwiches; the options go on. Since ...

How to Make Challah: A Step-By-Step Guide for Beginners

Challah is the one bread that you enjoy looking at almost as much as you enjoy eating. This classic eggy, ...