In large bowl combine yeast with 2/3 cup of water and 1 tbsp of the sugar. Let rest 5-10 minutes or until it is foamy.
Add in the rest of the water, sugar, honey, oil, eggs, salt, and about 4 cups of the flour. Beat to mix well.
Mix in raisins.
Using a stand mixer or by hand, slowly mix in enough flour to form a soft dough that is slightly sticky.
Cover with plastic wrap and let rest about 5 minutes.
Knead the dough by hand or use a dough hook of a stand mixer (on low speed). Knead the dough for about 10 minutes or until smooth and shiny. If needed, add sprinklings of flour to keep it from being too sticky. If kneading by hand, make sure to knead on a floured surface.
Roll dough into a ball and place in a well-oiled large bowl. Turn the dough over once to make sure all sides are oiled. Cover with a kitchen towel to create a dark, warm, environment, and allow to rest for 1-2 hours or until doubled in size.
Punch down the dough a few times to remove air bubbles, and then split the dough into two halves. Cover each half lightly with plastic wrap and let sit for 10 minutes.
Make cinnamon mixture by combining cinnamon, oil, and brown sugar.
Divide each half into the number of strands you want for your braid. Add cinnamon mixture to each strand. You can either spread it on top and braid that way, or pinch the dough around the cinnamon mixture to 'lock' it in.
Braid strands to form challah loaf. Once finished, transfer to a baking sheet lined with parchment paper. Cover with a kitchen towel and allow to rise for 45-60 minutes.
Preheat oven to 350° F.
Beat a large egg to create the egg wash. Brush onto top of challah loaves. If you would like, add some cinnamon sugar on top of the egg wash.
Bake for 40-45 minutes or until golden brown and the loaf sounds hollow when you knock or tap it.
Allow challah to cool on a cooling rack.