Pumpkin Challah Cinnamon Rolls Recipe

Decadent and delicious, this challah variation is the autumn comfort food of your dreams.

This recipe needs very little introduction, because it is just so decadent and delicious: Pumpkin challah. Cinnamon rolls. Sweet glaze. This is the autumn comfort food of your dreams. Or at least mine.

You can use this method to make cinnamon rolls using any flavor or recipe of challah you like. Just roll out your dough, schmear it with softened butter (or margarine), cinnamon sugar and roll it up to bake.


It’s gooey, spicy and the pumpkin flavor is delightful but not overwhelming. If you are looking for a brighter orange color, you could actually replace the pumpkin puree with sweet potato puree. The taste and consistency will be almost identical.

I recommend serving these sweet rolls with a nice cup of tea or coffee, a big comfy chair and relaxing dose of foliage watching.


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 tsp cinnamon

½ tsp ground ginger

¼ tsp nutmeg

¼ tsp ground cloves

1 tsp vanilla

2 large eggs

For filling:

1 ½ cups brown sugar

1 ½ Tbsp cinnamon

½ tsp ground cloves

¼ tsp salt

¾ cup (1 ½ sticks) butter, at room temperature

For glaze:

2 cups powdered sugar

¼-1/3 cup milk

1 tsp vanilla

Pinch salt


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.

In a large bowl or stand mixer fitted with whisk attachment, mix together 1 1/2 cups flour, salt, sugar  and spices. After the water-yeast mixture has become foamy, add to flour mixture along with oil, vanilla and pumpkin puree. Mix thoroughly.

Add another cup of flour and eggs until smooth. Switch to the dough hook attachment if you are using a stand mixer.

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.

Place dough in a greased bowl and cover with damp towel. Allow to rise 3-4 hours.

Preheat oven to 350 degrees. In a medium bowl mix together brown sugar, cinnamon, cloves and salt for filling.

Grease two 9×13 pyrex dishes. You could also use round cake pans.

Split dough evenly into two balls. I like using a kitchen scale to be as precise as possible, though this isn’t necessary.

Roll out each ball of dough into a large rectangle about ½ inch thick. Spread half the softened butter all over. Top with half the brown sugar mixture. Roll up on the longer side, working quickly. Pich dough together and pinch ends.

Cut dough into roughly 2 inch pieces.  Place in greased baking dish. Repeat with other half of dough.

Allow the cinnamon rolls to rise another 30 minutes. Place a damp towel over rolls while rising.

Bake around 20-23 minutes, or until rolls appear puffy and no longer raw or too doughy in the middle.

While rolls are baking, whisk together powdered sugar, milk, vanilla and pinch of salt in a small bowl.  If glaze seems too thick/too thin add milk or powdered sugar until desired consistency.  Drizzle on top of challah rolls using a spoon while rolls are still warm so glaze melts slightly.

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