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Plum and Rosemary Challah
Photo credit Sonya Sanford

Plum and Rosemary Challah

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A sweet and savory challah made in the round and perfect for Rosh Hashanah.

  • Total Time: 4 hours 30 minutes
  • Yield: 2 loaves 1x


Units Scale

For the challah dough:

  • 1 ¼ cups lukewarm water (100-110ºF)
  • 2 (¼ oz) packets active dry or instant yeast (4½ tsp)
  • ¾ cup + ½ tsp granulated sugar, divided
  • 5 cups bread flour, preferably King Arthur, divided, plus more for dusting
  • 2 ½ tsp kosher salt
  • ¼ cup vegetable oil, plus more for the bowl
  • 3 large eggs, divided
  • 24 Tbsp sesame seeds, poppy seeds, nigella seeds, flaky or coarse salt, or everything bagel seasoning (optional)

For the filling:

  • plum jam, as needed (see recipe below)
  • 34 large sprigs fresh rosemary, chopped
  • 2 Tbsp turbinado sugar

For the plum jam:

  • 2 lb plums
  • 1 cup sugar, or to taste
  • juice of ½ a lemon


  1. Start by making the dough: Place 1¼ cups lukewarm water in a small bowl. Sprinkle with 2 packets active dry or instant yeast and ½ tsp of the granulated sugar, and stir to combine. Let sit until foamy on top, about 5 minutes. If it doesn’t smelly “yeasty” or bubble up, throw it out and start again with new yeast. Meanwhile, place 1½ cups of the bread flour, the remaining ¾ cup granulated sugar and 2½ tsp kosher salt in the bowl of a stand mixer.
  2. When the yeast is ready, mix the flour mixture with the whisk attachment on medium speed until combined, 1-2 minutes. Add the water-yeast mixture and ¼ cup vegetable oil and mix on high speed until smooth, about 3 minutes.
  3. Stop the mixer and switch to the dough hook attachment. Add the remaining 3½ cups bread flour and 2 of the large eggs. Mix on high speed until the dough is smooth and pulling away from the sides of the bowl, about 5 minutes.
  4. Lightly coat a large bowl with vegetable oil and transfer the dough into the bowl. Cover the bowl with a damp kitchen towel or plastic wrap. Let rise in a warm place until doubled in bulk and puffy, about 3 hours at room temperature, or overnight in the refrigerator.
  5. To make the plum jam (optional): Slice the plums, discarding the pits. To a medium pot, add the plums, 1 cup of sugar and the lemon juice. Bring the mixture up to a boil, and lower it to a simmer. After 5 minutes carefully taste the hot mixture, if you would like it sweeter, add more sugar, ¼ cup at a time. I prefer to keep this jam more tart than sweet, as the challah will likely be dipped in honey. Simmer the jam for 35-45 minutes or until easily coats the back of a spoon and has substantially thickened and reduced; it will continue to thicken as it cools. Allow the jam to fully cool before using.
  6. If the challah dough has been refrigerated, let it sit at room temperature for 1 hour. Line a baking sheet with parchment paper or a silicone baking mat.
  7. Transfer the dough onto a very lightly floured work surface. Divide into 2 portions (about 22 oz each). 
  8. Divide half of the dough into the 4 equal-sized pieces, or into the number of strands you intend to braid with. Roll out each piece of dough into a long rectangular shape, about 12” long and 3-4” wide. Add 1-2 tsp plum jam to the center of the dough. Top the jam with a sprinkle of chopped rosemary. Fold over the dough and firmly seal it shut, then roll the dough into a long strand. If the strand splits a little, just press it closed again; minor splitting will not be a problem. After filling each strand, braid your challah. Repeat the process with the remaining half of the dough. 
  9. Transfer the braided challahs to the baking sheet, spacing them evenly apart. Let the challah rise uncovered until risen by about ½ inch and puffed, 25-35 minutes. This step is very important to ensure a light and fluffy challah.
  10. Meanwhile, arrange a rack in the middle of the oven and heat the oven to 375ºF. Place the remaining 1 large egg in a small bowl and beat with a fork to break up.
  11. Brush the egg wash liberally over the challah. Sprinkle each loaf with 1-2 Tbsp chopped rosemary, and 1 Tbsp turbinado sugar, if desired. 
  12. Bake until the challah is golden on the outside and sounds hollow when you “knock” on the bottom, 24-28 minutes. Transfer to a wire rack and let cool completely before serving or freezing.


Once the plum jam is fully cooled, store in the fridge for up to 1 month, or in the freezer for longer. Jam can be made in advance of the challah, and is best made at least 1 day ahead of time. If you need to cool it quickly, place in the freezer for 15-20 minutes. 

  • Author: Sonya Sanford
  • Prep Time: 4 hours
  • Cook Time: 25-30 minutes
  • Category: Side Dish
  • Method: Baking
  • Cuisine: Holiday