Cinnamon Apple Stuffed Challah

Love challah? This Cinnamon Apple Stuffed Challah was made for Rosh Hashanah! For Pomegranate Beet Challah, Pumpkin Challah and more, check out the challah index.

Happy Jew Year! (Bwahaha that never gets old.) As I mentioned last week, I absolutely LOVE fall! Apple and pumpkin picking, Halloween, snazzy blazers, riding boots, leaves changing all sorts of pretty colors, day drinking football…it’s all too good! I just hope it gets below 100 degrees one of these days. A girl can dream.

I am especially obsessed with fall flavors. I stock up on cranberries, pumpkin, cinnamony spices- I just can’t get enough! Now I have made challah before, but I wanted to take it to a higher level, so I took a leap of faith and swirled some sweet apples right on in. Holy amazing! And just perfect for Rosh Hashanah. Better late than never I guess.

Some of you (okay mostly just my Mom) asked to see a photo of me in my school uniform. Here you go! Me with my new slightly darker hair with my boyfriend Luke.

Oh and as an update on my winnings, I just won the Homesick Texan cookbook! I cannot tell you how excited I am- I’ll make sure to Jew up some recipes for the blog!

Now let’s make some challah of your very own. This recipe takes time, but I promise you can do it!

First, you want to make your yeast slurry. Whisk together yeast, 1/2 cup flour and warm water until smooth. Then walk away for 10 minutes until it puffs up. Easy! Next up, whisk eggs, oil, vanilla, sugar, salt and cinnamon into the yeast until it’s all incorporated.

Good so far? Great! Next up, a fun part (I mean this is all fun of course, but a really fun part.) Add the remaining two cups of flour and mix up with your hands until you get a shaggy ball (hehe).

The fun just doesn’t stop! Now knead your ball (hehe) for about 5-10 minutes. You can add some water if it is tough or flour if it is sticky. Then put your ball in a warm, clean bowl and cover with plastic wrap. Let it ferment for one hour until it puffs up.

While the dough is fermenting, you can get your apples ready. Peel and quarter your apples and cut into small pieces. Then mix with cinnamon and sugar. Oh yeah! Still with me? Good! Divide your dough into three pieces and roll each one out into a flat piece on parchment paper as so. Sprinkle some apples on one end of the piece.

Now roll the piece up tightly the long way making sure you don’t make any air bubbles. Repeat with your other dough blobs. Voila! Starting in the middle, braid your strands together. Youtube has some crazy awesome challah braiding recipes. It also has this video. Jew are welcome.

Nearly there! Now, transfer parchment paper with challah onto a baking sheet and cover again with plastic wrap. Let your challah proof another hour and a half until tripled in size. While your challah is proofing, preheat your oven. Glaze with another egg and bake for 35 minutes.

Shalom! This challah is awesome for all sorts of occasions- such as Rosh Hashanah. Or lunch. Can you guess which tasty recipe I made with it?

Check out this cross section! Next time I am definitely using more apples. I will probably add more as I roll up the pieces. If you try this, let me know how it turns out! You could also sprinkle more sugar on the outside before baking.

L’shana Tova!

Cinnamon Apple Stuffed Challah
Prep time
Cook time
Total time
A tasty sweet apple challah perfect for Rosh Hashanah!
Recipe type: Bread
Cuisine: Jewish
Serves: 12
  • 1 envelope instant yeast
  • 2½ cups bread flour
  • ½ cup warm water (100 degrees)
  • 2 eggs for the dough and 1 egg for an egg wash
  • ¼ cup vegetable oil
  • 1 tsp vanilla
  • 1 tsp cinnamon for the dough and 1 tsp cinnamon for the apples
  • ¼ cup plus 1 tablespoon sugar for the dough and 1 tsp sugar for the apples
  • 1 teaspoon salt
  • 2 apples, washed, peeled and diced into ½ inch pieces (I used Golden Delicious)
  1. Whisk yeast, 1 tablespoon sugar, and ½ cup of flour with warm water (100 degrees) into a slurry. Let it sit for 10 minutes until puffy.
  2. Mix in two eggs, oil, vanilla, 1 tsp cinnamon, ¼ cup sugar and salt into the yeast until all mixed.
  3. Then add the rest of the flour and mix with your hands into a shaggy ball.
  4. Knead dough for about 10 minutes until smooth; add more water if it is tough or flour if it is sticky.
  5. Put the dough in a clean and warm bowl and cover with plastic wrap. Let it ferment for one hour until puffy.
  6. Peel and chop up your apples into ½ inch sized pieces and sprinkle with remaining cinnamon and sugar.
  7. Once dough is ready, divide into three sections and roll each one out into a flat piece on parchment paper. Sprinkle some apples at one end and roll up the long way making sure to avoid air bubbles.
  8. Repeat with other dough balls.
  9. Braid up the strands starting in the middle and put your challah on a sheet pan lined with parchment paper.
  10. Cover with plastic wrap and ferment another hour and a half until it is triple the size.
  11. Preheat oven to 350 F.
  12. Wash challah with last egg and bake for 35 minutes until golden brown.
  13. Serve with honey!
Prep time includes fermenting time.




  1. Bubbe says

    Shana Punim!!!!!!!!!!!!!! You have the most adorable face-and to see you in your chef attire almost makes my faint heart stop beating. The Challah Fairy in New York has some very stiff competition!!! Keep up the great work!!!

    Your loving Bubbe

  2. says

    This looks wonderful. Sounds like a perfect way to use up some apples from our trees. Thanks for sharing the recipe. Btw, the Tzatziki dressing sounds great and easy to make!
    Oh, and I received the Rice goodies that I won. Thanks again for doing the giveaway! :o)

  3. Steve2inLA says

    Just found this site and Shofar, so good! On the challah, wonder if you wouldn’t get a smoother crumb with minced or shredded apples? That way, no structurally damaging holes. I’ll keep following if Jew keep cooking!

    • says

      Shofar, so good- bwahahaha I LOVE that! Definitely stealing that. Good idea on the challah- I really like the big chunks in there, but a smaller cut could add an overall apple flavor to the whole bread. Thanks for reading, Steve!

  4. Gillian says

    Didn’t see where to add cinnamon and sugar to the apples in the directions so forgot to do it until after I had already finished braiding. Might sprinkle cinnamon sugar in top of egg wash instead. Hope it works. P.s. you should fix the directions.

    • says

      Hi Gillian- sorry for the confusion! It had that step in the ingredients and blog post, but I made it more clear. I’m sure it will come out great! That just adds a little extra flavor to the apples.