On Rosh Hashanah, the Jewish New Year, it’s traditional to eat sweet foods like apples dipped in honey or date syrup (silan) to symbolize a sweet new year. As children, we learn a song that goes, “Dip the apple in the honey, make a bracha (blessing) loud and clear, L’Shana Tovah U’Metuka, have a happy sweet New Year!” Another tradition I love is eating round foods, which represent a crown or the cyclical nature of the years — one ending and a new one beginning.
This cinnamon raisin challah is perfect for Rosh Hashanah, but it’s a treat you can enjoy year round, especially if you love sweet challah and the ooey-gooey brown sugar that caramelizes at the bottom of the pan as it bakes. If you’re not a fan of raisins (though I can’t relate!), feel free to leave them out. The challah will still be delicious — perhaps even more so for you without those raisins you loathe. For my fellow raisin-lovers, feel free to use any color raisins you enjoy.
Notes:
- This challah crown can be stored at room temperature for up to 3 days in a paper bag, bread box, wrapped in plastic wrap, or in food storage bags.
- It can be frozen for up to 3 months, tightly wrapped in plastic wrap or foil. To defrost, remove the challah crown from the freezer and thaw at room temperature for 3-4 hours.
Text and images excerpted with permission from “Eat Jewish” by Melinda Strauss, published by Rock Point, (c) 2025.
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Cinnamon Raisin Challah Crown
Perfect for your High Holiday table.
- Total Time: 3 hours
- Yield: 2 loaves
Ingredients
For the dough:
- 1 ¼ cups (300 ml) warm water
- 1 Tbsp (9 g) active dry yeast
- 1 tsp (4 g) granulated sugar
- 2 large eggs, beaten
- ¼ cup (60 ml) + 1 tsp neutral oil, divided
- 1 tsp (5 ml) vanilla extract
- 4 ½ cups (610 g) bread flour + more as needed
- ½ Tbsp (9 g) kosher salt
For the filling:
- ½ cup (100 g) packed light brown sugar
- 2 Tbsp (30 ml) neutral oil
- ½ Tbsp (4 g) ground cinnamon
- sprinkle of kosher salt
- 1 cup (150 g) raisins
For the topping:
- ½ cup (100 g) granulated sugar
- 1 Tbsp (8 g) ground cinnamon
- 1 large egg, beaten
Instructions
- Make the dough: In a large bowl with a wire whisk, or the bowl of a stand mixer fitted with the whisk attachment, add the warm water, yeast and 1 tsp (4 g) granulated sugar and whisk to combine. Set aside for the yeast to activate, about 10 minutes; the top will be frothy when it’s ready.
- Add the eggs, ¼ cup (60 ml) oil and the vanilla to the yeast mixture. Whisk until fully combined, 10-15 seconds by hand or at low speed with the stand mixer.
- Add the flour and salt. With a rubber spatula or the stand mixer fitted with the dough hook attachment, mix until no flour is showing and a thick, shaggy dough is formed, about 2 minutes by hand or at low speed in the stand mixer.
- If kneading by hand, lightly flour a clean work surface and turn the dough out onto it. Knead the dough by pressing down with the heel of your hand and stretching it away from you; turn the dough about 45 degrees, fold it back toward you, then press and stretch it again. Repeat until smooth and elastic and no longer sticky, about 10 minutes. If using a stand mixer, set the speed to medium-low and mix until it’s smooth and elastic, and no longer sticking to the sides of the bowl, about 5 minutes. If the dough is sticking to your hands or the sides of the bowl, add up to ¼ cup (30 g) more flour, a little at a time.
- Brush the dough with the remaining 1 tsp oil to prevent sticking and transfer it to a clean large bowl. Cover the bowl with a clean kitchen towel and let it rest in a warm area until the dough has doubled in size, about 1 hour and 30 minutes.
- Meanwhile, make the filling: In a small bowl, add the brown sugar, 2 Tbsp oil, cinnamon and salt and stir to form a thick paste. Add the raisins and stir until evenly coated.
- Preheat the oven to 350°F (175°C/gas 4) and line two baking sheets with parchment paper.
- Turn out the dough onto a lightly floured surface. Using a bench scraper or sharp knife, cut the dough into 8 even pieces (about 6 oz, or 170 g, each) and form each one into a ball. Using a rolling pin, roll out the balls of dough into 3 by 12-inch (7.5 by 30 cm) strips, about ¼ inch (6 mm) thick.
- Spoon about 1 Tbsp of filling onto each strip and spread into an even layer. Bring together the long edges of the dough, and pinch together to enclose the filling inside. Roll the strips into logs.
- Make the topping: In a small bowl, add the ½ cup (100 g) granulated sugar and 1 Tbsp (8 g) cinnamon and stir to combine. Transfer to a plate. Roll the logs in the cinnamon-sugar mixture until they are fully coated.
- Braid the challah: On one of the prepared baking sheets, place two of the strands next to each other vertically, leaving 1 inch (2.5 cm) between them. Place two more strands perpendicular to the vertical strands, creating a # shape. Weave the two horizontal strands over and under the vertical strands. For each pair of ropes, cross the under strand over the over strand, moving counter-clockwise around the center and forming four new pairs of ropes. Now, moving clockwise around the center, cross the under strand over the over strand for each pair. Repeat moving counter-clockwise and then clockwise until you’ve used up all the dough. Tuck the ends underneath the loaf. Cover with a clean kitchen towel and set aside until the braids are puffed up and pillowy, about 30 minutes. Repeat with the remaining dough strands to make a second crown.
Photo courtesy of “Eat Jewish”; image design by Grace Yagel
- Brush the tops of the strands with the beaten egg. Bake until the top is golden brown and the challah is firm and springy to the touch, 25-30 minutes. Tap the bottom of the challah crown; it should sound hollow. Let cool slightly on the pans, about 10 minutes, then transfer the challah crowns directly onto a wire cooling rack to cool completely, about 1 hour.
Notes
- This challah crown can be stored at room temperature for up to 3 days in a paper bag, bread box, wrapped in plastic wrap, or in food storage bags.
- It can be frozen for up to 3 months, tightly wrapped in plastic wrap or foil. To defrost, remove the challah crown from the freezer and thaw at room temperature for 3-4 hours.
- Prep Time: 30 minutes + 2 hours rising time
- Cook Time: 25-30 minutes
- Category: Bread
- Method: Baking
- Cuisine: Jewish
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