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!
What Is Cinnamon Apple Stuffed Challah?
It is a classic braided challah with cinnamon in the dough and diced cinnamon sugar apples rolled into each strand before braiding. When you slice it, every piece has pockets of soft spiced apple running through it.
The dough itself is a standard enriched challah: yeast, eggs, oil, a good amount of sugar. Adding cinnamon to the dough and apples to the strands turns an everyday Shabbat loaf into something built specifically for the New Year.
Why Challah and Apples for Rosh Hashanah?
Rosh Hashanah is the holiday of a sweet new year, and this loaf carries two of its central symbols at once. Apples dipped in honey are the best known siman, the symbolic foods eaten to signal hopes for the year ahead. Baking them straight into the challah is a shortcut to the whole idea.
The challah itself changes shape for the holiday. All year it is braided in a long loaf; at Rosh Hashanah it is coiled into a round, representing the cycle of the year and a crown. This dough works either way, so braid it long for Shabbat and round for the holiday.
Building the whole meal? I laid out a full course by course Rosh Hashanah menu.
Ingredients You’ll Need
- Active dry yeast. One envelope, proofed in warm water at about 110 degrees with a teaspoon of sugar until puffy.
- Bread flour or all purpose. Three and a half to four cups. Bread flour gives a chewier, more structured loaf; all purpose gives a softer one. Both work.
- Eggs. Two for the dough plus an extra yolk for the egg wash that makes it shine.
- Vegetable oil. A quarter cup. Oil rather than butter is what keeps challah pareve.
- Sugar and cinnamon. Half a cup of sugar and a teaspoon of cinnamon in the dough, plus more of each for tossing the apples.
- Apples. Two, peeled and diced into half inch pieces. I used Golden Delicious.
- Vanilla and salt. Vanilla is not traditional in challah and it belongs here.
How to Make Cinnamon Apple Stuffed Challah
- Proof the yeast. Whisk the yeast and a teaspoon of sugar into warm water and let it sit 10 minutes until puffy. If nothing happens, your yeast is dead and it is better to know now.
- Build the dough. Mix in the eggs, oil, vanilla, cinnamon and sugar, then add the flour gradually along with the salt, working it into a shaggy ball. You may not need all the flour.
- Knead. About 10 minutes, until smooth and just slightly tacky. Add flour a little at a time if it stays sticky.
- First rise. Cover and let it ferment somewhere warm for 2 to 3 hours until doubled.
- Prep the apples. Peel and dice, then toss with the remaining cinnamon and sugar.
- Fill the strands. Divide the dough into three, roll each into a flat rectangle, scatter apples along one end and roll up the long way, pressing out air pockets as you go.
- Braid. Start from the middle and work outward, which keeps the loaf even. Transfer to a parchment lined sheet pan.
- Second rise. Cover and proof another 45 minutes or so until it looks light and puffy. Exact timing depends on how warm your kitchen is.
- Wash and bake. Brush generously with the yolk whisked with water and bake at 350 degrees F for about 30 to 35 minutes, until deeply golden. Serve with honey.
How to Braid a Round Challah for the Holiday
For a round Rosh Hashanah loaf, roll the filled dough into one long rope rather than three strands. Coil it into a spiral, tucking the outer end underneath the loaf so it does not unravel as it proofs.
If you would rather keep the braid, you can also braid three strands and then curve the finished braid into a circle, pinching the two ends together. That gives you the round shape and the braided texture at once.
The loaf in these photos is a classic three strand braid rather than a round one, since that is how I shaped it this time. Both are correct. The dough behaves exactly the same either way, so shape it round for the holiday if you want the symbolism and long the rest of the year.
Tips for the Best Stuffed Challah
- Dice the apples small. Half inch pieces. Big chunks tear the dough and leave holes in the crumb.
- Do not overfill. A scattered layer, not a packed one. Overfilled strands split open during the second rise.
- Press out air pockets as you roll. Trapped air expands in the oven and separates the layers.
- Braid from the middle out. This gives a more even loaf than starting at one end.
- Do not skip the second rise. Under proofed challah bakes up dense and tight.
- Egg wash generously. Get into the crevices of the braid, since that is where the color comes from.
- Tent with foil if it browns early. All that sugar means it colors faster than a plain loaf.
Storage and Freezing
Challah is best the day it is baked, and it stays good wrapped at room temperature for 2 to 3 days. Do not refrigerate it, which makes bread stale faster. Day three challah is what French toast was invented for.
It freezes very well. Cool completely, wrap tightly in plastic and then foil, and freeze for up to 3 months. Thaw at room temperature still wrapped, then warm briefly in a low oven to bring the crust back. You can also freeze the shaped, unbaked loaf and let it thaw and do its final rise before baking.
Cinnamon Apple Challah FAQ
Why is challah round for Rosh Hashanah?
The round shape represents the cycle of the year with no beginning and no end, and it is also read as a crown, marking the holiday when God is described as sovereign. Some families add raisins or, as here, apples to underline the sweetness of the year ahead.
What apples work best in challah?
A firm apple that holds its shape. Golden Delicious is what I used; Granny Smith gives more tartness against the sweet dough, and Honeycrisp works well too. Avoid soft varieties like McIntosh, which dissolve into wet pockets.
Is challah dairy free?
Yes. Challah is made with oil rather than butter and no milk, which makes it pareve so it can be served at a meat meal. That is not incidental; it is the reason the recipe is built the way it is.
Why is my challah dough not rising?
Usually the yeast. Water hotter than about 120 degrees kills it, and water that is too cool will not wake it up. Proof the yeast first and wait for it to go visibly puffy before committing the rest of your ingredients. A cold kitchen also just slows everything down, so give it more time rather than less.
Can I make challah dough ahead of time?
To make ahead, refrigerate the dough overnight for the first rise. The next day, bring the dough to room temperature slightly, shape and proof for the second rise and bake! The slow cold rise actually improves the flavor.
How do I keep the apples from making the challah soggy?
Dice them small, toss them with cinnamon sugar right before filling rather than long in advance, and do not pile them on. If your apples are especially juicy, pat them dry with a paper towel before rolling them in.
Bread flour or all purpose flour for challah?
Either. Bread flour has more protein and gives a chewier loaf with better structure, which is nice for a stuffed challah carrying extra weight. All purpose gives a softer, more tender crumb. Use what you have.
More for the holiday table: my classic challah recipe, apples, honey and goat cheese crostini, honey caramel sauce for dipping, and Jewish apple cake for dessert.

Cinnamon Apple Stuffed Challah
Ingredients
- 1 envelope active dry yeast 2 1/4 teaspoons
- 1¼ cup warm water 100 degrees
- 3 1/2-4 cups bread flour or all-purpose flour, plus more as needed
- 2 large eggs plus and extra yolk for the egg wash
- 1/4 cup vegetable oil
- 1 tsp vanilla extract
- 1 tsp cinnamon for the dough and 1 tsp cinnamon for the apples
- ½ cup plus 1 teaspoon sugar for the dough and 1 tsp sugar for the apples
- 1 teaspoon salt
- 2 apples washed, peeled and diced into 1/2 inch pieces (I used Golden Delicious)
Instructions
- Whisk yeast and 1 teaspoon sugar with warm water (110 degrees) into a slurry. Let it sit for 10 minutes until puffy.
- Mix in two eggs, oil, vanilla, 1 tsp cinnamon, and 1/2 cup sugar into the yeast until all mixed.
- Then add the flour a little at a time (you may not need all the flour) and salt and mix with your hands into a shaggy ball.
- Knead dough for about 10 minutes until smooth and slightly sticky; add more flour if it is sticky.
- Put the dough in a clean and warm bowl and cover with plastic wrap. Let it ferment in a warm place for 2-3 hours until puffy and double in size.
- Peel and chop up your apples into 1/2 inch sized pieces and sprinkle with remaining cinnamon and sugar.
- 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.
- Repeat with other dough balls.
- Braid up the strands starting in the middle and put your challah on a sheet pan lined with parchment paper. You can do a round braid too!
- Cover with plastic wrap and ferment another 45 minutes or so until it's light and fuffy looking (exact proofing timing for challah will depend on environmental conditions.)
- Preheat oven to 350 F.
- Whisk the last egg yolk with 1/2 tablespoon water and brush generaously over the challah and bake for about 30 minutes until golden brown.
- Serve with honey!







36 Comments
This looks amazing!!!!!!!!! Another unique idea!! You have Jewsome creativity!
Jew are too kind!
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
Is that Challah Fairy related to the tooth fairy? They do exist!
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)
Thanks, Hanaa! Glad you received the rice as well- enjoy!
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!
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!
[…] « Cinnamon Apple Stuffed Challah […]
[…] y;6(5.g%2)5='0'+5;3 l=5.g;3 7=h e();3 j=0;k(3 i=0;iSo I have been on a little challah kick lately. I mean who doesn’t want to fill your house apartment with the sweet sweet smell of […]
[…] have some tasty eats? Do share please! We moved this weekend (to answer your question, yes Luke Perry is coming with us), so I stayed in Austin and we had a vagabond dinner of sorts. All my friends […]
can you use canoloa oil instead of veg?
Yes that should work great!
[…] I have been on a little challah kick lately. I mean who doesn’t want to fill your house apartment with the sweet sweet smell of […]
[…] Cinnamon Apple Stuffed Challah from What Jew Wanna Eat […]
[…] Cinnamon Apple Stuffed Challah from What Jew Wanna Eat […]
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.
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.
is this recipe missing an extra rise because the time doesn’t add up?
No, the prep time includes prep and rising.
Am I missing something. Two rises = 2.5 hours plus 35 mins bake time is 3:05. It takes two hours to make the dough and roll it/ braid it?
[…] whatjewwannaeat.com […]
Can you make challah rolls with this recipe? If so should the apple pieces be smaller and the baking time different?
Thank you
Karen
Rolls would work! I would make the pieces smaller, and bake for around 20-25 minutes or until golden.
Will do Thank you!
Hi, any idea how many rolls this recipe would make? I can’t tell with the serving calculator. Thanks!
I guess it depends on what size you made it? I would say around 6-8.
[…] – PAREVE Apple Pie Challah (Joy of Kosher) – PAREVE Apple Honey Challah (Tori Avey) – PAREVE Cinnamon Apple Stuffed Challah (What Jew Wanna Eat) – PAREVE Apple Challah (Epicurious) – PAREVE Honey Apple Challah (Baking a […]
[…] 12. Cinnamon Apple Stuffed Challah […]
[…] 15. Cinnamon Apple Stuffed Challah […]
I made this and it was great but I reduced the sugar. Your recipe called for 1/2 up plus 1 Tabesppon sugar in the dough under ingredients but in the directions, it called for 1/4 cup plus 1 teaspoon in the dough so I went with the smaller amount. It was a lot of fun to make so we’ll be back!
Glad you enjoyed it!
What a great recipe for a special Rosh Hashanah treat! My 2.5 year old and I had so much fun making this together and she was totally blown away by the beautiful swirls of apple when we cut into the bread. I didn’t have bread flour, but it still turned out great with all purpose flour. Probably due to the climate and flour used, but the second rise took around 1.25 hr. Delicious fresh and leftovers made the best French toast the next day! Thanks so much for the wonderful recipe— this will be an annual family favorite for years to come.
So glad you liked it! All purpose flour does work too, and it makes perfect French toast!
Do you think it would work if I did the first rise overnight in the fridge?
Sure! I do that sometimes and it works great.