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Bread day is the best day, and these chocolate cherry pistachio challah rolls are exactly why. Each roll backs up tender and soft, with a glossy crust and a sprinkle of sesame seeds.




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What makes this recipe special
Time for some challahhhh! Excuse my excitement, but when it's time to make bread, there's a part of me that starts jumping for joy. Whenever people find out that I'm a professional chef, they always ask what my favorite dish to make is. Instead of a dish, my favorite thing to prepare is, without a doubt, bread. The process is long and requires patience, but the end result is (almost) always worth it.
That also applies to these chocolate cherry pistachio challah rolls. Wanting a sweet bread, I decided to take a basic challah recipe and incorporate chocolate, dried cherries, and toasted pistachios. Not only are these challah rolls beautiful, but they also taste as good as they look!
Recipe
Chocolate Cherry Pistachio Challah Rolls
Ingredients
Dough
- 1 cup warm water, between 100-110 degrees F (250 ml)
- 1 ½ tablespoons active dry yeast (15 grams)
- 3 tablespoons olive oil (35 grams)
- ¼ cup granulated sugar (50 grams)
- 2 large eggs
- 1 large egg yolk
- 1 ½ teaspoons salt
- 4 cups all-purpose flour (592 grams)
Filling
- ½ cup butter, softened (113 grams)
- ½ cup granulated sugar (100 grams)
- ⅓ cup unsweetened cocoa powder (27 grams)
- 1 tablespoon orange zest
- 4 ounces bittersweet chocolate, chopped
- ¾ cup toasted pistachios, chopped (100 grams)
- ¾ cup dried cherries, chopped (120 grams)
Remaining ingredients
- egg wash (1 large egg beaten with 1 tablespoon water)
- 2 tablespoons sesame seeds
Instructions
- Make the dough. Combine warm water with active dry yeast. Stir to combine and let sit for 5 minutes or until the mixture is foamy.
- Pour the yeast mixture into the bowl of a stand mixer. Add the olive oil and sugar and beat to combine. Add the eggs and egg yolk one at a time, mixing to combine. With the mixer on, gradually add the salt and flour. Switch the dough hook and knead the dough until smooth, about 7-8 minutes. If the dough is still sticky, add 1-2 tablespoons of additional flour. Transfer the dough to a clean bowl, cover and let proof in a warm area for 1 ½ hours or until doubled in size.
- Meanwhile, make the filling. Beat together the softened butter with sugar and cocoa powder until well combined. Chop the pistachios, dried cherries, and chocolate.
- Punch down the dough and divide it into 10 equal portions. Roll out each of the portions into a large circle about 7 inches in diameter. Spread about 1 tablespoon of the cocoa butter mixture in an even layer on the dough and sprinkle the chocolate, pistachios, and dried cherries on top. Roll up the dough into a log, closing the seam.
- To shape the challah rolls, roll out the log until it's about 12 inches long. Shape the log into an upside-down U. Then, take the left end of the roll and overlap the right end. Take the end that is now on the right side and pull it up towards the center hole. Take the remaining left side and pull it back towards the center, pinching the two open ends together. Arrange the challah roll on a lined baking sheet and repeat with the remaining portions.
- Brush egg wash on the rolls, loosely cover and proof for 1 more hour in a warm area.
- Preheat oven to 375 degrees F.
- Brush egg wash once more on the proofed rolls. Sprinkle sesame seeds on top and bake for 18-20 minutes or until golden brown. Remove from the oven and let cool completely. Enjoy!
Notes
Step-by-step instructions
Step 1: Make dough
If you have ever made challah before, this chocolate cherry pistachio challah recipe should be familiar. Even if you haven't, don't be intimidated! Making bread can be a very rewarding and soothing experience.
Let's dive right in and make the dough. Challah is a fairly simple dough. It's kosher bread, so that means there's no dairy in the dough; however, there are eggs in the bread, which gives the bread a rich flavor.

Activate the yeast by mixing it with warm water. Combine the yeast water mixture with olive oil and sugar. Then, add the eggs, mixing until combined.
With the mixer on, slowly add the flour and salt to the wet ingredients. Don't add all of the flour at once, or else it won't incorporate with the wet ingredients. Once all of the flour has been added, knead the dough until smooth.
Cover the dough and let it proof for about 1 ½ hours or until doubled in size.
Step 2: Prepare filling
While the dough is proofing, prepare the filling. Chocolate, cherry, and pistachios are a beautiful combination. But if you're not a fan of pistachios, you can use any other type of nuts, such as hazelnuts, almonds, or pecans.
You can also swap out the dried cherries for cranberries, raisins, or even dried blueberries.

Beat together the softened butter with sugar and cocoa, and chop up the pistachios, dried cherries, and chocolate.
Step 3: Shape rolls
Punch down the dough and divide it into 10 equal portions. Take each portion and roll it into a 7-inch circle.
Then, spread about 1 tablespoon of the chocolate butter mixture and sprinkle the toppings on top. Roll up the dough into a log and pinch together the seams to close them up.

Now it's time to shape the challah rolls. Take the log and shape it into an upside-down U. Grab the right end and cross it over the left side.
Next, take the right end and loop it through the little hole.

Take the left side of the log and fold it back so that it connects with the side you just looped through the hole. Pinch those two ends together to close the seam.

If all of this seems like too much work, feel free to make one large braided loaf instead.

Lay all of the challah rolls on a lined baking sheet and brush the tops with egg wash. Lightly cover the rolls and proof them for another hour.
Step 4: Bake
When it's time to bake, brush another layer of egg wash on top of the rolls and sprinkle sesame seeds on top. Then, bake the chocolate cherry pistachio challah rolls for about 18-20 minutes or until beautifully browned.
Remove the rolls from the oven and let them cool completely. You can serve the rolls warm or at room temperature.

If you want to freeze some of the rolls, wait until they cool completely, then wrap them tightly and place them in the freezer. The rolls should last two months in the freezer.
These chocolate cherry pistachio rolls were almost too pretty to eat. But just almost! I'll admit, the chocolate is the main flavor of this sweet bread, but every once in a while, you'll bite into a sweet dried cherry or get the texture of the pistachios. And it's quite lovely.
For another fantastic chocolate bread recipe, check out these nutella stuffed almond pretzel bites!

Make-ahead and storage
- Make-ahead: You can make the dough the night before and store it in the refrigerator overnight. Let it come to room temperature the following morning before shaping.
- Store: Keep the bread in an airtight container in the refrigerator for up to 3 days.
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Maura Shapiro says
Is it possible to make this in 1 regular braid challah instead of individual rolls?
Christine Ma says
Absolutely! It will take much longer to bake so you'll have to adjust the baking time, though.