16 Rolls

VIDEO: How to Make Pumpkin Challah Cinnamon Rolls

These gooey rolls are a sinful combination of flavors and smells.

The smell of ooey gooey cinnamon rolls is likely one of the most intoxicating smells on earth. Butter, cinnamon, sugar and dough make a sinful combination of flavors and smells.

But at The Nosher you know we like to put on our own Jewish spin even on classics, which is why we are here to share your new favorite autumn brunch recipe: pumpkin challah cinnamon rolls. This recipe is as simple as making a great challah dough, adding pumpkin puree and spice and then rolling it into some decadent, butter and sugar filled rolls. Top it all off with a simple glaze, and you have spiced heaven on a plate.

Serve it for brunch, serve it on lazy holiday and Sunday mornings. And don’t expect too many leftovers.

Note; This recipe makes around 16 rolls. If you want to freeze half, hold off on the glaze. Freeze after the rolls have cooled and then add glaze to the second batch only after defrosted and warmed through slightly.


For the dough:

1 ½ Tbsp yeast

1 tsp sugar

1 1/4 cup lukewarm water

4 ½- 5 cups unbleached all-purpose flour (I prefer King Arthur brand)

¾ cup sugar

¼  cup vegetable oil

½ cup pumpkin puree (not pumpkin pie filling)

½  Tbsp salt

1 heaping tsp pumpkin pie spice

¼ tsp ground cloves

1 tsp vanilla

2 large eggs

For filling:

1 ½ cups brown sugar

1 Tbsp cinnamon

1/8 tsp ground cloves

¼ tsp salt

1 cup (2 sticks) unsalted butter, at room temperature

For glaze:

2 cups powdered sugar

¼-1/3 cup milk

1 tsp vanilla

Pinch salt


  1. In a small bowl place yeast, 1 tsp sugar and lukewarm water. Allow to sit around 5-10 minutes, until it becomes foamy on top.
  2. In a large bowl or stand mixer fitted with whisk attachment, mix together 1 1/2 cups flour, salt, sugar, pumpkin pie spice and cloves. After the water-yeast mixture has become foamy, add to flour mixture along with oil, vanilla and pumpkin puree. Mix thoroughly.
  3. Add another cup of flour and the eggs until smooth. Switch to the dough hook attachment if you are using a stand mixer.
  4. Add another 1-1 ½ cups flour and then remove from bowl and place on a floured surface. Knead remaining flour into dough, continuing to knead for around 5 minutes. Don’t add more flour then the dough needs – the less flour, the lighter the dough.
  5. Place dough in a greased bowl and cover with damp towel. Allow to rise 3-4 hours.
  6. Preheat oven to 350 degrees. In a medium bowl mix together softened butter, brown sugar, cinnamon, cloves and salt for filling.
  7. Grease two 8- or 9-inch round pans (you could also use one large rectangle pyrex dish if preferred).
  8. Split dough evenly into two balls. I like using a kitchen scale to be as precise as possible, though this isn’t necessary.
  9. Roll out each ball of dough into a large rectangle about ½ inch thick. Spread half the softened butter-sugar mixture all over. Roll up on the longer side, working quickly. Pinch dough together and pinch ends.
  10. Cut dough into roughly 2-inch pieces.  Place in greased baking dish. Repeat with other half of dough.
  11. Allow the cinnamon rolls to rise another 30 minutes. Place a damp towel over rolls while rising.
  12. Bake around 25 minutes, or until rolls appear puffy. slightly brown and no longer raw or too doughy in the middle.
  13. While rolls are baking, whisk together powdered sugar, milk, vanilla and pinch of salt in a small bowl.  If the glaze seems too thick/too thin add milk or powdered sugar until desired consistency.  Using a spoon, drizzle glaze on top of challah rolls while the rolls are still warm so the glaze melts slightly.

Keep on Noshing

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