Combine remaining sugar and flour in a large mixing bowl. Add 2 cups of flour one half cup at a time and mix until uniform. This ensures that the flour and sugar are completely combined.
Make a well in the center of the flour and pour the yeast mixture in the well. Stir to combine and it turns into a sticky dough.
Take one third of the dough and mix in the pumpkin, salt, pumpkin pie spice. Now continue to add one more cup of flour until the dough resembles the texture in the photograph of the dough above.
For the remaining dough, mix in the vanilla and chocolate chips with the dough hook attachment for the stand mixer. Blend until the dough firms up, approximately 3 to 5 minutes.
Form the pumpkin dough into ball and on well-floured surface, knead it for approximately 3 minutes, or until it's a firm solid ball. Add a bit more flour if necessary. Kneading will firm the dough up, so don't add too much more flour. Repeat with the chocolate chip dough. .
Put the pumpkin dough and the chocolate chip dough in slightly greased bowls and cover with a towel. Let the dough rise in a warm area of your house for 40 minutes. The dough should double in size.
Lightly grease (vegan butter works best) a long baking sheet.
Punch the dough down and divide the chocolate chip dough into two equal pieces. Knead all three balls of dough for two minutes each and then roll into 16 to 18 inch ropes.
Place all three ropes next to each other with the pumpkin roll in the center and braid the dough into a large loaf.
Place the dough on the baking sheet and cover with the towel. Let rise for another 40 min.
Preheat oven to 350°F (176°).
Bake for approximately forty minutes, or until the bread is a light golden brown. .