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Weigh 630g of the flour; or measure 5 1/4 cups by gently spooning it into a cup, then sweeping off any excess.
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In the bowl of a stand mixer fitted with the dough hook or in a large bowl, mix the flour, sugar, yeast, salt, and cinnamon to combine.
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In a small bowl or liquid measuring cup, whisk the water, pumpkin, oil, and egg to combine.
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Add the wet ingredients to the dry ingredients and mix until a shaggy dough forms, about 1 minute. Scrape the sides of the bowl.
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Knead the dough for about 6 minutes on medium speed if using a stand mixer, or about 10 minutes if kneading by hand, working in the remaining 1/2 cup (60g) flour a little at a time, until an elastic, slightly tacky dough forms.
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If you kneaded the dough in the stand mixer, cover the bowl. If you kneaded the dough by hand, transfer it to a lightly greased bowl and cover. Allow the dough to rise for about 2 hours, or until it has doubled in bulk.
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Lightly grease a baking sheet or line it with parchment. Set aside.
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Gently deflate the dough and transfer it to a lightly greased or floured work surface.
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Divide the dough in half (about 620g each). Working with one piece at a time and leaving the second piece covered, pat or roll out the dough into a large rectangle, about 12" x 5" in size.
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Starting with one of the long edges, tightly roll up the dough (think cinnamon-roll-style) so you end up with a long rope of uniform thickness. Pinch the seam to seal.
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Use the palms of your hands to roll the dough log gently from the center outwards 2 to 3 times to lengthen it to a 24" rope.
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Transfer the dough to the prepared baking sheet, loosely coiling it like a snail, leaving room for the dough to expand, then tucking the end under the coil. (Avoid coiling the dough too tightly; a tight coil will rise upward, as opposed to outward, during baking.)
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Repeat with the other piece of dough and place it on the baking sheet at least 3" away from the first loaf.
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Cover the shaped loaves with lightly greased plastic or your favorite reusable wrap and let them rise at room temperature until puffy, about 1 hour.
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While the dough is rising, preheat the oven to 350°F with a rack in the center.
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Brush the risen loaves with egg wash. Wait a couple minutes, then apply a second layer of egg wash. You will not use all the egg wash, but applying 2 layers results in a very shiny, deeply golden exterior on the baked loaves.
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Bake the loaves for 35 to 40 minutes, or until they’re deep golden brown and a digital thermometer inserted into the center of each reads 190°F.
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Transfer the loaves to a cooling rack and allow them to cool completely before slicing.
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Store leftover pumpkin challah, well-wrapped, at room temperature for up to 3 days or in the freezer for up to 3 months.