2 medium loaves

Balsamic Apple Date Challah for Rosh Hashanah

When you break into the round loaf, it is like biting into a challah cinnamon bun.

I love a good challah challenge and always welcome an excuse to create new flavors for friends and family to try. I tend to favor savory combinations such as rosemary and garlic, za’atar and “everything bagel” challah flavors, although I also make salty chocolate and cinnamon raisin versions on occasion.

For Rosh Hashanah this year I wanted to branch out and try something completely new and perfect for the holiday.

A few months ago I was chatting with my husband’s best friend’s mother, whom we lovingly call “Mama Morley.” She was explaining a technique she uses for round challah that I had not tried before – stuffing the challah dough and rolling it like a cinnamon bun. Brilliant!

This conversation stuck in my head, and so as I was mulling over potential recipes for the New Year I realized I should try this technique and stuff it with something uniquely delicious for Rosh Hashanah.

And thus my Balsamic Apple Date Challah was born. The dough itself is sweet, laced with cinnamon, vanilla and just a touch of nutmeg. And when you break into the round loaf, it is like biting into a challah cinnamon bun.


I sprinkled the top of the challah with thick sea salt, cinnamon and sanding sugar. But you can leave the salt off if you would rather go all-sweet. Either way, your guests will barely be able to control themselves around this challah. My daughter kept trying to sneak her own bites, as you can see below from her chubby little hands which somehow made it into the photos.

Wishing everyone a sweet, happy, healthy and DELICIOUS New Year.



For the challah dough:

5 cups flour

½ cup sugar

2 Tbsp honey

½ Tbsp salt

2 tsp vanilla

1 tsp cinnamon

¼ tsp nutmeg

¼ cup vegetable oil

1 ½ Tbsp yeast

1 tsp sugar

1 ¼ cups lukewarm water

2 whole eggs

1 egg yolk

For the filling:

3 gala apples, peeled and diced

1 cup pitted dates, chopped

½ tsp salt

1 cinnamon stick

¼ cup water

¼ cup red wine

2 Tbsp balsamic vinegar

1 Tbsp sugar

For top of challah:

1 egg

1 tsp water

1 tsp honey

1 Tbsp sanding sugar

1 Tbsp thick sea salt

2 tsp ground cinnamon


In a small bowl, place yeast, 1 tsp sugar and lukewarm water. Allow to sit around 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, honey, vanilla, cinnamon and nutmeg. After the water-yeast mixture has become foamy, add to flour mixture along with oil. 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 1/2 cups flour and then remove from bowl and place on a floured surface. Knead remaining flour into dough, continuing to knead for around 10 minutes (or however long your hands will last).

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

To make the filling, place apples, dates, salt, cinnamon stick, water, red wine and sugar in a medium saucepan and bring to a boil. Continue to simmer on medium heat until the mixture is reduced. Add the balsamic vinegar and simmer another 2-3 minutes. The mixture will cook around 10-15 minutes in total.

Remove from the heat and allow to cool 5 minutes. Remove cinnamon stick.

Place mixture in a food processor fitted with a blade attachment and pulse until smooth.

After the challah is done rising, cut the dough in half. To be as precise as possible, use a scale to measure the weight.

Roll the first ball out using a rolling pin into a rectangle. Spread around half, perhaps slightly less, of the apple-date mixture in an even layer, leaving 1/2 inch all around without filling. Working quickly, start rolling up the dough towards you. Try and keep the roll relatively tight as you go. Pinch the end when you finish.

Create a pinwheel shaped-challah by snaking the dough around and around in a circle around itself. When finished, tuck the end under the challah neatly and pinch lightly. This doesn’t have to be perfect – remember, as long as it tastes good, almost no one (maybe except that judgmental great aunt) will care what it looks like.

Repeat with other half of dough.

Preheat the oven to 350 degrees.

Allow challahs to rise another 30-60 minutes, or until you can see the the size has grown.

Beat 1 egg with 1 tsp water and 1 tsp of honey. Brush liberally over each challah. Combine sea salt, sanding sugar and cinnamon, and sprinkle over challah.

Bake for 25-30 minutes, or until middle looks like it has just set, and the color is golden.

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