For the challah dough:

  • 4 1/2-5 cups King Arthur bread flour
  • ½ cup sugar
  • 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

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, beaten + 1 tsp honey
  • thick sea salt (optional)
  • cinnamon sugar (optiona)

Make the dough

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.


Make the filling

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.


Shape loaves

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.


Glaze and Bake

Preheat the oven to 350 degrees.

Allow challahs to rise another 30-45 minutes, or until you can see the the size has grown. Beat 1 egg with 1 tsp of honey. Brush liberally over each challah. Top challah with thick sea salt and cinnamon sugar if desired.

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