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Everything is Better With Chocolate

When my mom visited Los Angeles, right before all of the Covid craziness began, she gave me a cookbook called Rage Baking that is an anthology of women’s writings on feminism and recipes to support them. While my mom was in town, I made Grace Young’s Chocolate Cherry Biscottti, because really, who doesn’t love the combination of chocolate and cherry?? This challah is a riff off of the classic flavor combination in Grace’s biscotti.


4 ½ Teaspoons instant yeast (2 packets of active dry yeast works too but I have found instant yeast results in a fluffier texture)

¾ Cup sugar

2 large eggs, beaten

1 Teaspoon kosher salt

1 Tablespoon orange zest

½ cup margarine, melted

7 cups all-purpose flour ( I typically use anywhere from 6-8 cups of flour depending on the temperature and humidity outside)


½ Cup Hershey’s special dark cocoa powder

2 Teaspoons brown sugar

1 Teaspoon white sugar

1 Teaspoon orange zest

2 Tablespoons melted butter

1 Cup dried tart cherries roughly chopped (I like trader Joe’s dried pitted tart montmorency cherries)

Whisk eggs, salt, ½ cup shortening, ¾ cup sugar, 2 cups warm water, yeast, and orange zest in a large bowl.

Add the beaten eggs and flour one cup at a time to yeast mixture. Using a strong spatula to mix at the beginning and using your hands to mix once it gets too difficult with the spatula.

Once the dough is fully mixed, turn onto a floured surface and knead for ten minutes. (If you don’t knead the dough well enough, the challah will not hold its shape when it is braided.)

Grease a large bowl with spray oil and transfer the dough to the bowl. Cover with a damp paper towel and put in the oven to prove. (Make sure the oven is off!) Proof until the dough is doubled in size about 45 minutes-1 hour.

While the dough is proving, make the filling by adding all ingredients except for butter to a medium sized bowl. Melt butter in a saucepan over medium heat. Add into the bowl and mix to combine. If the filling is too dry, feel free to melt a little more butter and add to filling.

Once proved, turn the dough onto a floured surface and cut into 6 equal portions. Keep three portions out and place three back into the bowl.

Roll each portion into a long rectangle. Spread the filling evenly over the rectangle leaving about ⅓ inch on every side. Tightly roll the rectangle so that it creates a long rope and pinch the seam tightly so that it does not explode in the oven. Repeat for each of the other portions of dough, saving a little bit of the filling to top the challah with before baking.

Using your palm, press the three ropes together at the top and begin to braid the dough. Once finished braiding, tuck each of the ends under to create a more finished/clean look. Do the same with the remaining three pieces of dough. Let proof for another 30 minutes.

Preheat oven to 325 degrees. While the oven is heating beat one egg with a splash of water to create an egg wash. Using a pastry brush, brush the egg wash over the top of the loaves. Bake the loaves for 15 minutes, then increase the temperature to 425 degrees. (Keep an eye on the loaves once you up the temperature, you may have to cover them with tinfoil if the tops start to get too dark.)

Continue baking for another 15-20 minutes until the loaves sound hollow when you tap on the bottom.

NOTES: Do not try to slice the bread right when it comes out of the oven. If you are storing the bread to eat later, make sure it is fully cooled before you put it into any kind of container or it will create condensation that will lead to mold.

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