Stuffed Dessert Challah (Photo/Faith Kramer)
Stuffed Dessert Challah (Photo/Faith Kramer)

Celebrate Sukkot abundance with this stuffed dessert challah

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Abundance and plenty are themes for Sukkot foods, and this Stuffed Dessert Challah has plenty of abundance. The golden bread is packed with nuts, raisins and chocolate, making it a sweet choice to enjoy inside the sukkah.

Sukkot this year begins at sundown Sept. 20 and lasts for eight days in the diaspora, seven in Israel.

This challah is shaped by crisscrossing alternating strips of dough. Try it with other fillings and toppings. Substitute your own challah recipe, if desired.

Stuffed Dessert Challah

Serves 8

  • 1⅛ tsp. (half package) active dry yeast
  • ½ tsp. plus 1 Tbs. sugar
  • ¼ cup warm water
  • 2 large eggs
  • 2 Tbs. plus 1 Tbs. water
  • 1 Tbs. oil plus extra
  • ¾ tsp. salt
  • 1½ to 2 cups of bread flour plus extra
  • Challah filling (see below)
  • Cinnamon sugar

Stir yeast and ½ tsp. sugar into ¼ cup warm water, let rest until foamy. Separate one egg and reserve yolk. Beat white with remaining egg in large bowl. Stir in oil, remaining sugar, salt and 2 Tbs. water. Stir in yeast mixture.

Gradually add 1½ cups flour. Mix until a rough, tacky (not sticky) dough is formed, adding  flour or water by spoonful as needed. Turn out onto a lightly floured work surface. Knead about 12 minutes, until a pinch of dough feels resilient and firm.

Place dough in a greased bowl. Turn to coat. Cover with dish towel until doubled. While dough is rising, beat egg yolk with 1 Tbs. water for egg wash and refrigerate. Make filling (see below). Line baking sheet with parchment paper. Lightly oil paper.

When dough has doubled, punch down, remove from bowl, and knead briefly on lightly floured surface. Use floured rolling pin to shape into a long rectangle or oval that’s roughly 7 or 8 inches by 12 or 13 inches. If the dough resists shaping, let it rest 5 to 10 minutes and try again.

Use a knife to lightly mark (do not cut through) the filling zone, a 3-inch band in the center with about a 1½-inch margin at the short ends and about a 2-inch margin on the long sides.

Mound the filling in the “zone” so it covers the whole area and is 1½ inches high at the top of the mound.

Take a knife and cut strips about ¾ inches apart along one of the long sides, cutting from almost the edges of the filling zone to the outside edges. Do the same for the other long side, making the same number of strips.  Leave the 3-inch center of the short edges uncut, but cut angled ¾-inch strips in the remaining area of the short edges (from the long edges up to the center zone).

Finishing the challah is sort of like wrapping a mummy. Start at a short end of the dough. Crisscross the angled strips from one end to the other, stretching them so the strips touch the opposite side. Next, alternate crisscrossing the straight strips. Alternate from edge to edge, stretching each strip to touch the opposite side. Leave the two “end caps” for last. Fold them up over the ends, stretching to tuck edges under the challah.

Heat oven to 350 degrees. Move challah to baking sheet and cover with dish towel for 30-45 minutes until a knuckle pressed into the dough leaves a small indent. Brush challah with egg wash. Sprinkle with cinnamon sugar. Bake for 25 to 30 minutes, until golden or an instant-read thermometer inserted in the bread (not filling) reads 190 degrees. Cool on rack before slicing.

Challah filling: Mix ¼ cup plus 2 Tbs. roughly cut walnuts, ¾ cup roughly chopped raisins, ¼ cup plus 2 Tbs. semisweet chocolate chips, ½ tsp. cinnamon and 1 tsp. sugar.

Faith Kramer
Faith Kramer

Faith Kramer is a Bay Area food writer and the author of “52 Shabbats: Friday Night Dinners Inspired by a Global Jewish Kitchen.” Her website is Contact her at [email protected].