In a small bowl or measuring cup, sprinkle yeast and granulated sugar on warm water. Stir. Let stand for up to 10 minutes (it should look like the foam on beer).
In a large bowl, combine oil, brown sugar, salt, eggs, pumpkin puree, and then the yeast mixture. Stir in the cinnamon and nutmeg, then 3 cups of flour.
Gradually stir in most of the remaining flour. Dough will be sticky. *The amount of flour used will vary, depending upon the moisture in the air.
Place dough on lightly floured surface and knead for 5 minutes (or use a standing mixer with the dough hook on a low speed), adding a little flour at a time as needed. If dough sticks to the counter, use a bench scraper to clean the surface and lightly flour the board to prevent further sticking. When done kneading, the dough will feel silky and smooth.
Put dough into a lightly greased bowl, cover with plastic wrap and let rise for 1½ hours in a warm, draft-free environment until approximately doubled (the bowl placed inside your oven with the light on is a good spot).
Punch down the dough with your floured fist. Shape as you like or follow instructions for shaping into pumpkins below.
Place dough on parchment paper or nonstick baking mat. Preheat the oven to 375°F. Cover the dough with plastic wrap or a clean dish towel as it goes through the final rise for 30 minutes to 1 hour. Note: If you are pressed for time, you can skip the second rise and still get great results!"
Right before baking, brush the bread with beaten egg wash (egg and water).
Baking times:
Two large pumpkins: bake for 15 minutes and then remove the pan from the oven (shut the oven door so the heat does not escape). Brush with additional egg wash and rotate the pan when returning it to the oven. Bake for another 15 minutes.
16 pumpkin rolls: bake for 12 minutes and then remove the pan from the oven (shut the oven door so the heat does not escape). Brush with additional egg wash and rotate the pan when returning it to the oven. Bake for another 10-12 minutes.
Note: The bread should take approximately 30+/- minutes in total, until golden brown and challah sounds hollow when bottom is tapped. (Internal temperature approximately 190°F - 195°F) Temperature will vary depending on the size of the bread.
Allow the bread to rest and cool for one hour before a) removing the kitchen twine, if making pumpkins, and b) serving.
If making large pumpkins, place a cinnamon stick in the center of each loaf to resemble the stem.