High Holy Days Challah

By Peter Fritz

All year long our challah is braided, but it is round for Rosh Hashanah. What does the challah’s shape teach us about this special time of year?

There are many explanations. Round challahs have no end, symbolizing (and actualizing) our wish for a year in which life and blessings continue without end. Round challahs represent the circle of life and mark the cyclical nature of the passage of a year, a reflection of the continuing cycle of years and seasons. Togetherness, a hugging circular grip comes to mind. When I connect the end of a braid to the beginning, I think of it as symbolizing the end of one year flowing into the beginning of a new year.

During this time, we are to be introspective, looking back as we plan ahead, taking stock of all that has transpired and endeavoring to make resolutions to continue to better ourselves as human beings. Our thoughts turn to repentance and self-improvement, the round challah reminds us that the opportunity for teshuvah, return, is never-ending.

Date, Walnut, Silan, and Sesame Challah

The round, braided challahs of the Jewish High Holidays are special, and filling the strands of those braids makes them even more so. Here, the combination of plump Medjool dates, date molasses and walnuts makes a filling that is rich and surprisingly not too sweet. Use other nuts if you like, but we think this flavor trio — graced with nutty-tasting sesame on top — is a winner.

If you have a 9 1/2-to-10-inch springform pan, use it to bake this challah; it will help keep the bread’s shape.

Make Ahead: The dough needs to proof twice: first for 1 hour, and again for 30 to 40 minutes after the dough has been filled, braided and shaped into a pan. The baked challah can be wrapped in aluminum foil, then plastic wrap, and frozen for up to 1 month. To reheat, discard the plastic wrap but keep the bread wrapped in foil; warm through in a 350-degree oven for 10 to 15 minutes.

Where to Buy: Silan, often labeled date molasses, is available in Mediterranean markets. You can find roasted sesame seeds in the international aisle (Asian section) of large grocery stores.


For the challah

  • 1 cup lukewarm filtered water, plus 1/2 to 1 cup filtered water
  • 1/2 cup sugar
  • 3 packets (3/4 ounce) active dry yeast
  • 34 ounces (scant 8 cups) all-purpose flour, plus more for the work surface
  • 3 teaspoons kosher salt
  • 1/2 cup canola oil, plus more for proofing
  • 4 teaspoons date molasses (silan; see headnote)
  • 2 large eggs, plus 2 large eggs for the egg wash
  • Roasted sesame seeds, for garnish

For the filling

  • 16 tablespoons silan
  • About 6 ounces walnut halves, chopped (2 scant cups)
  • About 12 ounces Medjool dates, pitted and chopped into 1/2-inch pieces (2 packed cups)


For the challah: Whisk together the lukewarm water, 1/2 teaspoon of the sugar and all the yeast in a liquid measuring cup. Cover tightly with plastic wrap; let stand for about 20 minutes, until a head of bubbles forms and the mixture increases in volume.

Combine the flours, the remaining sugar and the salt in the bowl of a stand mixer fitted with a dough-hook attachment; beat on low speed for about 10 seconds, then add the yeast mixture, the 1/4 cup of oil, the silan and 1 egg. Gradually add the remaining 1/4 to 1/2 cup water (as needed); the dough will seem a bit wet, initially. Beat for 10 minutes (low), during which time the dough will firm up and become elastic; stop once or twice to work the dough down the hook as needed.

Use some oil to lightly grease a proofing bowl. Transfer the dough to the bowl, making sure to turn the dough so it’s evenly coated, cover with plastic wrap and set in a non-drafty place for 1 hour or until the dough doubles in volume.

Lightly flour a work surface. Uncover the dough and plop it out onto the surface. Use a bench scraper or large knife to divide the dough into 4 equal portions. Working with one at a time, roll out each portion to a rectangle that’s about 12 inches long and 8 inches wide, checking to make sure it isn’t sticking to the surface.

Filling: Spread 2 tablespoons of silan evenly over each rectangle of dough, leaving a 1/2-inch margin at the edges. Scatter one-quarter each of the chopped dates and walnuts evenly over the silan. Starting with the long edge of the dough that’s closest to you, tuck and roll the dough, making sure to blend in the seam at the end. The 4 filled rolls of dough should be the same length and of even thickness, so adjust them as needed.

Line the springform pan or a baking sheet with parchment paper.

To braid the dough, think woven tic-tac-toe grid or hashtag as the first step.

Place 2 filled-dough ropes horizontally (parallel with the edge of the countertop) with no more than 1/2 inch between them. Place a third filled rope of dough perpendicular toward the middle of the pair of horizontal ropes. Weave it over the top horizontal rope and under the other horizontal rope. Place the fourth filled rope parallel and to the left of the third rope with 1/2-inch space between; weave it under the top horizontal strand and over the bottom horizontal strand. That should create the desired hashtag pattern, with the remaining ropes extending beyond it.

Working clockwise, bring the under rope of dough (in each pair) over the next one. Then, working counterclockwise, do the same, with each next pair of ropes. Bring the rope that is in the “under” position up and over the next rope that is in the “over” position. Pinch each new pair of rope ends and twist; tuck them underneath the now-round, braided challah while cupping the dough with your hands to plump up the braids and finesse the round shape.

Support the underside of the woven round as you transfer the dough to the pan or baking sheet. Tuck and shape it in the pan as needed. Cover with a clean dish towel; let it proof in a non-drafty place for 30 to 40 minutes. Do not over proof, or the shape of the challah may be adversely affected.

Meanwhile, preheat the oven to 350 degrees. (If you like, set the proofing pan of dough atop the range while the oven preheats below.)

Once the dough has proofed a second time, beat the remaining egg well in a liquid measuring cup. Brush the top of the dough with the beaten egg, making sure not to let the egg drip down the sides (or the bread may stick to the sides of the pan), then immediately scatter the roasted sesame seeds over the top.

Bake (middle rack) for 50 minutes or until nicely browned and fragrant, rotating the bread from front to back about halfway through the baking time. Transfer the pan to a wire cooling rack; let cool for 20 to 30 minutes before removing the pan’s springform ring and bottom (if using). Cool the bread completely (keeping it on its parchment) before serving or storing.