Pesto is one of my favorite ingredients to stuff inside challah or babka. Because of the consistency of pesto, the flavors sort of infuse right into the dough as it bakes. Don’t feel you have to restrict yourself to classic basil pesto – I have improvised various versions of pesto made from whatever is local and fresh at my farmers’ market including kale, basil, spinach, garlic scapes, and even uber-trendy ramps. Note, this challah (as with all stuffed challahs) can either be made round or braided.
In a small bowl, place the yeast, half teaspoon sugar, and lukewarm water. Stir gently to mix. Allow to sit five to 10 minutes, until it becomes foamy on top.
In a large bowl or stand mixer fitted with the whisk attachment, mix together one and a half cups of the flour, salt, and the remainder of the sugar. Add the water-yeast mixture and oil to flour. Mix thoroughly.
Add another cup of the flour and two eggs and mix until smooth. Switch to the dough hook attachment if you are using a stand mixer.
Add another one and a half to two cups of the flour and mix thoroughly. Remove from the bowl and place on a floured surface. Knead the remaining half cup flour into the dough, continuing to knead for about five minutes.
Place dough in a greased bowl and cover with a damp towel. Allow to rise at least three hours, punching down at least once if possible.
When fully risen, split the dough into two parts.
Spread one-third of the pesto in the middle of each rope. Top each with one-third of the cheese. It may seem like a lot as you are doing it, and it will be messy, but the amount of filling can be deceiving.
Fold the sides of each rope up over the filling and pinch tightly. Roll slightly to even out the shape. Braid.
Working quickly, roll each rectangle from the longer end into a long rope. Try to keep the roll relatively tight as you go. Pinch the ends when you finish. Circle the dough around itself and then pinch under.
Place challahs on a baking sheet lined with Gefen Parchment Paper or a silicone baking mat. Allow challah to rise another 30 to 45 minutes, or until you can see the size has grown and dough seems light. Preheat oven to 375 degrees while the dough rises.
In a small bowl beat two egg yolks with one teaspoon water.
Brush the challah liberally with egg wash and top with dried basil and coarse sea salt. Bake for 24 to 26 minutes, or until golden brown.
To make a braided stuffed challah (see note for a variant): Split each dough section into three additional sections. Roll each into a rope about six inches long. Flatten the ropes.
Some stuffing may pop out on the top or sides; this is fine. The round turban challah (see below) may require one to two additional minutes of baking to ensure it is cooked through inside.
To make stuffed turban challah: Roll out each of the two sections of dough into a large rectangle using a rolling pin. Spread about half of the pesto in an even layer on each rectangle, leaving a ½- inch border all around. Top each with half of the cheese.
To make a braided stuffed challah: Split each dough section into three additional sections. Roll each into a rope about 6 inches long. Flatten the ropes.
Reprinted with permission from Modern Jewish Baker: Challah, Babka, Bagels & More by Shannon Sarna (Countryman Press, 2017). Photograph by Veronica Sage McAvoy. Click here to purchase.