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Baked Cinnamon Challah Bread
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5 from 6 votes

Cinnamon Challah Bread Recipe

This soft buttery bread comes with a brown sugar cinnamon swirl. You only need 11 ingredients and the rising time is just 45 minutes.
Prep Time30 mins
Cook Time30 mins
Rising45 mins
Total Time1 hr 45 mins
Course: Breakfast, Dessert
Cuisine: American
Keyword: challah recipe, cinnamon challah bread, how to make challah bread
Servings: 18 slices
Calories: 258kcal



  • ½ cup lukewarm milk (120ml)
  • ¼ cup granulated white sugar (50g)
  • 3 tbsp honey (64g)
  • 2 ¼ tsp active dry yeast (7g)
  • 2 large eggs
  • ½ cup butter, melted (113g)
  • 1 tsp cinnamon
  • 1 vanilla bean* (or 1 tsp vanilla extract)
  • 1 tsp salt
  • 3 ½ cups all-purpose flour (420g)

Filling and brushing

  • ½ cup butter, melted (113g)
  • ¾ cup brown sugar (150g)
  • 1 tbsp cinnamon
  • 1 large egg, beaten
  • 2 tbsp coarse sugar for sprinkling on top


  • In a large mixing bowl, using a stand or handheld mixer fitted with a whisk attachment, combine milk, sugar, honey, and yeast and stir to combine. Let sit for about 10 minutes until it starts to get foamy on the surface. 
  • Preheat oven to 200°F (100°C). Line a baking sheet with parchment paper. Set aside.
  • Add eggs, butter, cinnamon, vanilla*, and salt and whisk to combine. 
  • Replace whisk attachment and attach a dough hook. Add flour and stir on medium-low speed until the dough comes together about 3-5 minutes. The dough should be sticky to touch but should start to come off the sides of the bowl. If it doesn't come off the sides of the bowl, turn speed to low and add 1 tbsp of flour at the time until you reach this point. Don't add too much flour, stay at around 3+¾ cups (450g) flour highest.
  • Then turn on medium-high speed and knead for about 5 minutes. Transfer dough to a lightly greased heatproof bowl (brush a few drops of oil in a bowl or use a non-stick spray). Turn off the preheated oven and place the bowl in the oven to rise for about 15 minutes. Leave the oven door ajar. 
  • For the filling, stir together butter, brown sugar, and cinnamon until combined. Set aside.
  • Remove the bowl from the oven and preheat again to 200°F (100°C). Line a baking sheet with parchment paper. Set aside.
  • On a very lightly floured surface cut challah bread dough into 3 equal pieces. Roll each dough into a 16-inch (40cm) long and 5-inch (12cm) wide rectangle, about 0.15 inch (3-4mm) thick. Spread filling on top of each dough equally leaving a 1 - 1.25-inch (2-3cm) space around the edges. Starting at one long side, roll up each dough tightly, trapping the filling. Seal the edges with your fingers. Repeat with the two remaining dough pieces.
  • Place all 3 strands side by side. Pinch together the upper end of the 3 strands. Braid the strands, pinch the end and tuck the tip under that it has a round shape. Turn the loaf upside down that the top tip is facing to you and braid until fully braided. Then pinch the end and tuck the tip under. Transfer to the parchment paper layered baking sheet. Turn off the preheated oven and place it in the oven to rise for about 30 minutes. Leave the oven door ajar.
  • Remove the baking sheet from the oven and preheat to 375°F (190°C). Lightly brush the bread with egg and sprinkle with coarse sugar. Bake for about 30-32 minutes. Cover loosely with parchment paper or foil after 10 minutes to prevent heavy browning. Let cool for about 30 minutes. Although it is best eaten fresh, you can store it in an airtight container at room temperature up to 2 days.



*First, cut off the straight end of the vanilla bean. Then place the tip of your sharp knife below the curled end and cut the vanilla bean through the middle of the bean lengthwise. Although you don't need to cut it all the way through, it's ok when you do so. Then open the vanilla bean and scrape out the flavorful seeds with the back of your knife. Then just use the seeds.


Calories: 258kcal | Carbohydrates: 35g | Protein: 5g | Fat: 12g | Saturated Fat: 7g | Cholesterol: 59mg | Sodium: 238mg | Potassium: 73mg | Fiber: 1g | Sugar: 15g | Vitamin A: 371IU | Calcium: 32mg | Iron: 1mg