Ingredients
Units
For the challah dough:
- 4 ½–5 cups King Arthur bread flour
- ½ cup sugar
- ½ Tbsp salt
- 2 tsp vanilla
- 1 tsp cinnamon
- ¼ tsp nutmeg
- ¼ cup vegetable oil
- ¼ cup honey
- 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 (optional)
Instructions
- 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 1½ 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 1½ 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 ½ 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°F.
- 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.
- Prep Time: 20 minutes + 3 hours rising time
- Cook Time: 25 minutes
- Category: Rosh Hashanah
- Method: Baking
- Cuisine: Ashkenazi