Savory Tomato Stuffed Challah Bread

Shabbat Shalom!

I haven’t said that in years, but figured it would be appropriate to on a Friday morning. The last time I said Shabbat Shalom to someone was on a a Saturday afternoon to an observant couple walking down the streets of LA. I was never that observant growing up, but I do miss miss the tradition. The traditions of Friday night dinner, big Passover events and breaking apart freshly baked challah bread.

Baking challah is about the extent of my heritage tradition. I made my first challah just a year or so ago and probably made a really bad one when I was in Yeshivah school. The entire process is relaxing and so rewarding and really, the possibilities are endless. Of course, with the abundance of cherry tomatoes I’ve been hoarding, a savory tomato stuffed challah was certainly on my list of “crazy things to do”. I’ve never stuffed a challah before so this whole recipe was a combination of a whim experiment and selfishness, because…all things tomatoes..always!

I have to admit this turned out to be a gorgeous, bread. During baking, the seam that closed the tomatoes slightly opened up, exposing a huge head of roasted garlic and red cherry tomato. I love how beautifully rustic the bread turned out to be. This recipe makes 2 large loaves and I one stuffed with roasted tomatoes and the other I stuffed with sun-dried tomatoes.

Warning..I’ll be sharing LOTS of challah photos in this post!  This is what the challah looks like on the inside..gorgeous, isn’t it? As you braid the bread, the stuffing becomes intertwined and every piece you cut and each bite will have a stunning array of savory tomatoes and herbs.

And really…the possibilities are endless. If you don’t like tomatoes (and how can we be friends?) then how about just fresh herbs and cheese? I also have sweet stuffed ideas in my head…like a play on a cinnamon roll with brown sugar and pecans! Wouldn’t that be lovely for Thanksgiving?

What would you stuff your challah with?

Method:

1) In the bowl of a stand mixer, add 1 cup warm water, yeast and sugar. Mix lightly with a fork to get all the yeast in the water and set aside for about 15 minutes. It should begin to foam up and you should see little bubbles.

2) Next, add eggs, oil and honey and whisk together.

3) Using a dough attachment on your mixer, gradually add sifted flour and salt, about 1/2 cup at a time with the mixer on low. Continue to mix until everything is incorporated. The dough should begin to pull away from the bowl and come to 1 large ball of dough.

4) Turn the dough onto a very well floured surface and knead for about 5 minutes. You can use your finger to see if it’s ready. Press your finger in and if the dough bounces back quickly, it’s ready.

5) In a large bowl, pour a bit of oil in and place your dough ball in the bowl. Turn it around so the entire dough is covered with a thin layer of oil. Cover with a clean towel and place bowl in a warm spot. (for me, it was my oven). Allow to rest and rise for 1 1/2hours until doubled in size.

6) When dough is ready, it should have doubled in size. Punch the dough down and knead a bit to soften. Divide dough into 2 balls, this will be your challahs. Cover 1 ball of dough as you work with the other.

7) Divide dough into 3 pieces, this will be your braid strands.. Take 1 of the strands and roll making a long snake, about 15 inches long, but it should be thick enough to stuff, about 1-2inches thick. Use a rolling pin to flatten the strand.

8) Next use a teaspoon to fill the strand. Don’t overfill, leaving the ends along. Bring the strand together, pinching with your fingers and making sure no filling peeks out (but it’s ok it some does). Once strands are sealed, gently roll the strands and begin breading.

9) Line 3 strands together and pinch at 1 end. Braid a 3-sgrand bread and pinch the bottom end together.

10) Place on baking sheet and cover challah with a towel. Allow to rise for another 30 minutes.

11) When done, Brush challahs with egg wash and sprinkle with coarse sea salt and freshly chopped herbs.

12) Bake at 375 degrees F for 30 minutes then bring the temperature down to 350 degrees F for 10 minutes.

13) Allow to cool before cutting.

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Savory Tomato Stuffed Challah Bread

Recipe adapted and doubled from Foodologie

Servings: 2 large challah

Author: Samantha Ferraro

Ingredients

Challah

• 4 cups all purpose flour + more for kneading sifted
• 1 cup lukewarm water
• 1 packet yeast 1/4oz
• 1 Tb sugar
• 2 Tb honey
• 2 tsp kosher salt
• 1/4 cup vegetable
• 2 eggs + 1 yolk save white for egg wash
• Coarse sea salt + freshly chopped herbs for garnishing challah

Roasted Tomato Filling

• 1 pint cherry tomatoes
• 4-5 garlic cloves peel removed
• Olive oil for drizzling
• Salt and pepper to taste
• 1/2 cup feta crumbled
• Fresh herbs basil, rosemary, oregano, etc, chopped finely

Sun-dried Tomato Filling

• 1 cup feta crumbled,
• 1/4 cup sun dried tomatoes chopped
• Fresh herbs basil, rosemary, oregano, etc, chopped finely

Instructions

• In the bowl of a stand mixer, add 1 cup warm water, yeast and sugar. Mix lightly with a fork to get all the yeast in the water and set aside for about 15 minutes. It should begin to foam up and you should see little bubbles.
• Next, add eggs, oil and honey and whisk together.
• Using a dough attachment on your mixer, gradually add sifted flour and salt, about 1/2 cup at a time with the mixer on low. Continue to mix until everything is incorporated. The dough should begin to pull away from the bowl and come to 1 large ball of dough.
• Turn the dough onto a very well floured surface and knead for about 5 minutes. You can use your finger to see if it's ready. Press your finger in and if the dough bounces back quickly, it's ready.
• In a large bowl, pour a bit of oil in and place your dough ball in the bowl. Turn it around so the entire dough is covered with a thin layer of oil. Cover with a clean towel and place bowl in a warm spot. (for me, it was my oven). Allow to rest and rise for 1 1/2hours until doubled in size.
• When dough is ready, it should have doubled in size. Punch the dough down and knead a bit to soften. Divide dough into 2 balls, this will be your challahs. Cover 1 ball of dough as you work with the other.
• Divide dough into 3 pieces, this will be your braid strands.. Take 1 of the strands and roll making a long snake, about 15 inches long, but it should be thick enough to stuff, about 1-2inches thick. Use a rolling pin to flatten the strand.
• Next use a teaspoon to fill the strand. Don't overfill, leaving the ends along. Bring the strand together, pinching with your fingers and making sure no filling peeks out (but it's ok it some does). Once strands are sealed, gently roll the strands and begin breading.
• Line 3 strands together and pinch at 1 end. Braid a 3-sgrand bread and pinch the bottom end together.
• Place on baking sheet and cover challah with a towel. Allow to rise for another 30 minutes.
• When done, Brush challahs with egg wash and sprinkle with coarse sea salt and freshly chopped herbs.
• Bake at 375 degrees F for 30 minutes then bring the temperature down to 350 degrees F for 10 minutes.
• Allow to cool before cutting.

Challah Filling

• In a baking dish, toss together the cherry tomatoes, garlic, olive oil, salt and pepper and herbs until well coasted. Roast at 400 degrees F for about 15 minutes until tomatoes begin to blister and garlic is soft. Allow to cool and add crumbled feta and fresh herbs.
• For the sun-dried tomato challah, just mix those ingredients together. Taste for seasoning.

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