Stuffed Dessert Challah Embodies the Sukkot Harvest Theme of Bounty

The harvest theme of Sukkot always resonates with me. It is symbolic of abundance and plenty and holiday foods are often stuffed or overflowing to represent this motif. Other compelling draws are the potlucks and communal meals under the sukkah that we host or attend as we celebrate Sukkot.

This sharing of our bounty makes me think of Hadassah’s Youth Aliyah Villages, where Hadassah members from around the world help provide new immigrant youth and at-risk Israeli kids from a variety of countries and religious backgrounds with emotional, educational and psychological support.

Visit this link for more information about these Hadassah Youth Villages or to help support the work they do.

To bring this sense of bounty and shared community to my holiday table this year, I’m sharing my Stuffed Dessert Challah. The golden bread is packed with nuts, raisins and chocolate. The challah is shaped by crisscrossing alternating strips of dough. Substitute a vegan challah recipe (use one calling for about 2 cups of flour) and dairy-free chocolate chips if desired.

This year Sukkot begins the evening of October 6 and ends at nightfall on October 13.

Stuffed Dessert Challah
Serves 8

1 1/8 tsp. (half package) active dry yeast
1/2 tsp. plus 1 Tbsp. sugar
1/4 cup warm water
2 large eggs
1 Tbsp. plus 2 Tbsp. water
1 Tbsp. oil plus extra
3/4 tsp. salt
1 1/2 to 2 cups of white bread flour plus extra

Challah filling (see below)
Cinnamon sugar, purchased or homemade (see note)

Stir yeast and 1/2 tsp. sugar into 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 Tbsp. water. Stir in yeast mixture.

Gradually add 1 1/2 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 greased bowl. Turn to coat. Cover with a dish towel until doubled. While dough is rising, beat egg yolk with 1 Tbsp. 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 it from bowl and knead briefly on lightly floured surface. Use floured rolling pin to shape into a 7-to-8 inch by 12 -to-13 inch long rectangle or oval. If the dough resists shaping, let it rest 5-10 minutes and try again.

Use a knife to lightly mark (do not cut through) the filling zone, a 3-inch-wide band in the center, with about a 1 1/2 inch margin at short ends and about a 2-inch margin on long sides.

Mound the filling in the “zone” so it covers the whole area and is 11/2 inches high at the top of the mound.

Take a knife and cut strips about 3/4 inch apart along one of the long sides, cutting from almost the edge of the filling zone to the outside edge of the rectangle. 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 3/4-inch strips in the remaining area of the short edges from the long edges up to the center zone.

Finishing the challah resembles wrapping a mummy. Start at a short end of challah. 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 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 until doubled (or until a knuckle pressed into the dough leaves a small indent.) Brush challah with egg wash. Sprinkle with cinnamon sugar. Bake for 25-30 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 1/4 cup plus 2 Tbsp. roughly cut walnuts with 3/4 cup roughly chopped raisins, 1/4 cup plus 2 Tbsp. semisweet chocolate chips, 1/2 tsp. cinnamon and 1 tsp. sugar.

Note: To make your own cinnamon sugar, simply mix granulated white sugar with ground cinnamon. I like a mix that’s half and half. For a spicier, less sweet mix, use more cinnamon than sugar. For a sweeter, milder flavor, add more sugar than spice.

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Faith Kramer is a member of the Hadassah Writers’ Circle, a dynamic and diverse writing group for leaders and members to express their thoughts and feelings about all the things Hadassah does to make the world a better place. It’s where they celebrate their personal Hadassah journeys and share their Jewish values, family traditions and interpretations of Jewish texts. Hadassah members are proud of their Zionist mission and their role as keepers of the flame of Jewish values, traditions and beliefs as well as advocating for women’s empowerment and health equity for all. Since 2019, the Hadassah Writers’ Circle has published nearly 650 columns in The Times of Israel Blogs and other Jewish media outlets. Interested? Please contact hwc@hadassah.org.