Chocolate Challah

Jan Rood-Ojalvo
Recipe by
Jan Rood-Ojalvo

When my sister Debby asked me to create a chocolate challah, I decided to be bold. I wanted a loaf that smelled heavenly even as it was baking and tasted decadent from the first bite. The joy of challah is its crust, and this chocolate version is crusty on the outside, chewy on the inside, and studded with chocolate chips.

I had never mixed chocolate into bread dough before. I chose a good variety of cocoa to add generously as I mixed the dough, and even decorated the glazed braids with extra chocolate chips for stunning effect before sliding the loaves into the oven. I couldn't wait to try the result. It looked gorgeous and was simply delicious. This recipe will be a keeper in my family, and I hope in yours!

5 cups all purpose flour
1/2 cup granulated sugar
1 package active dry or instant yeast (2 1/2 teaspoons)
1/2 teaspoon salt
1/3 cup good quality unsweetened cocoa powder
2 tablespoons unsalted butter
2 egg yolks
1 cup semisweet chocolate chips, with extras for topping
1 3/4 to 2 cups milk (or water to serve with a nondairy kosher meal)
  • In a stand mixer, use the paddle attachment to mix flour, sugar, salt, yeast, cocoa and chocolate chips.
  • Warm the butter and milk in the microwave until just lukewarm, and pour gradually into the flour as it mixes at slow speed. Add one egg yolk (save the other for the glaze) and continue mixing. Change to the dough hook attachment and knead 5 minutes at medium speed. Or turn the dough out onto a floured counter to knead by hand for 5-10 minutes. Dough should be smooth and elastic. Feel free to add an extra tablespoon or so of water one at a time if needed to form a soft pliable dough.
  • Place dough in a greased plastic bag in the refrigerator overnight or up to 5 days. (Dough may also be frozen, then placed in fridge the night before baking.) When ready to bake, leave plastic bag on the counter to come to room temperature for at least one hour (and up to 4 hours).
  • With a sharp knife or dough cutter, divide dough into 2 (for large loaves) or 4 (for smaller loaves) equal pieces. Divide each piece into three parts, roll each into a rope (fat in the middle and tapered at each end), braid the three ropes into a braid and pinch tightly at each end. Place several inches apart on a greased baking sheet. Mix the second egg yolk with 1 tablespoon water. Brush each loaf with glaze. Place a dozen chocolate chips on top, tucking them gently into the seams.
  • Place loaves in a cold oven. Turn oven on to 375°F. The bread will rise as the oven heats, then move right into baking. Large loaves will take about 45-50 minutes, small loaves about 30 minutes, but the exact time depends on your oven. Loaves should feel crusty, bottom will be well browned and should sound hollow when tapped. If unsure, leave in an extra five minutes. 
  • Let cool briefly on rack. Enjoy!

Jan Rood-Ojalvo has longstanding ties to Congregation M'kor Shalom and the Katz JCC, both in Cherry Hill, NJ. Jan, who lives with her husband Steve in Haddonfield, NJ, loves baking, traveling, opera, and staying in touch with her six children – and two granddaughters.