This piece originally appeared in The Nosher.

I have been making challah for my family and friends forever, and I kept at it in 2020, when challah baking became a trend on social media. But as the year of quarantining progressed, I found myself looking for a way to shake things up a bit. 

Enter stuffed challah. I turned to the experts for guidance. Shannon Sarna, editor of The Nosher and author of Modern Jewish Baker, is a master challah baker. She stuffed her first challah seven years ago with a jam-like filling of apples, dates, and balsamic vinegar. “A lot of people took issue with what I was doing. They were offended and skeptical,” she shared. Eventually the concept caught on and was, says Sarna, “Embraced by more people.”

Challah baker and instructor Katja Goldman turns to her garden for inspiration, filling her dough with surplus pesto made from homegrown basil, or with figs and lemons from her fruit trees.

I learned from these two that you can be as creative as you like when stuffing your challah, but there are some caveats. Sarna warns that when adding water-heavy fruits or vegetables, compensate elsewhere in the recipe so that you don’t end up with soggy bread. And while filling is exciting, too much of it could leave you with an interior that is not properly baked. Experiment to find the right balance, says Sarna.

Goldman advised to leave a border around your stuffing when applying it to the flattened challah dough. The clean borders of dough will then be pinched together to hold the stuffing in place. When braiding, be sure to place the seam on the bottom of the bread, for a neat look.

These eight stuffed challahs have a bit of everything. They’re homey and familiar, with a delicious surprise nestled inside. And boy, we could all use that.

1. Balsamic-Apple-Date Challah

This challah started Sarna on her stuffed challah journey. She finds that you can get more stuffing into a round challah than in a braided version, in which you fill each strand.

2. Halvah Stuffed Challah

Food blogger and author Molly Yeh stuffs and decorates her challah with three types of sesame: tahini, a sesame paste; halvah, a sesame confection sweetened with honey; and sesame seeds that you sprinkle on top.

3. Fig, Olive Oil, and Sea Salt Challah

Deb Perelman of Smitten Kitchen makes a challah stuffed with figs, olive oil, and sea salt that’s not only hard to resist but “makes the finest French toast” she’s ever had. 

4. Sufganiyot Challah

Don’t have to wait ’til Hanukkah to prepare this one! Chef Michael Solomonov and Steve Cook’s recipe combines challah and sufganiyot into one delicious, jam-filled creation.

5. Poppy Seed Filled Challah

Goldman makes a bread that is a challah, bialy, and conversation piece, all rolled in one. It’s a filled challah that’s a work of art — you can even wear it!

6. Pomegranate and Beet Challah

This challah is a little bit sweet, a little bit tart, and altogether beautiful. And who wouldn’t want a pink-tinged challah?!

7. Pesto and Goat Cheese Stuffed Challah

Challah does not have to be sweet, it just needs to be special, and this savory stuffed challah by Shannon Sarna is exactly that. Put your preconceptions aside and dig in.

8. Woven Herb and Flower Challah

Erez Komarovsky, who food writer Adeena Sussman calls the “godfather of artisanal baking” in Israel, makes a stuffed challah of a different kind. His stuffing is on the outside. He braids his dough and then entwines herbs and flowers in the strands so that the challah is part bread, part bouquet, and completely beautiful.