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1. In a small saucepan over low heat, heat 1/4 cup of the milk and the 1 tablespoons of sugar until the sugar has disintegrated. Transfer to a small bowl. When the milk cools to 110u00b0F, sprinkle in the yeast. Set aside for about 20 minutes, for the yeast to rise and puff.
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2. In a small saucepan over medium heat, combine the remaining sugar and 1/4 cup milk, butter and salt and cook, stirring until everything is melted and well combined, about 5 minutes. Remove from the heat and transfer to the bowl of a standing mixer fitted with the dough hook.
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3. With the mixer on low, add in the pumpkin puree and mix until well incorporated. Add the egg and mix well. Add the yeast mixture.
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4. With the mixer running on low speed, add the flour, 1 cup at a time. After you have added all of the flour, increase the mixer speed to medium and keep mixing until you have a smooth dough, 3 to 4 minutes.
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5. Grease a large mixing bowl and transfer the dough to the bowl. Cover the top of the bowl with plastic wrap and put the bowl somewhere warm and draft-free for the dough to rise. Leave for at least 1 hour, and up to 3 hours.
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6. For the filling, melt the butter in a small saucepan over medium heat until melted. Set aside.
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7. On a lightly floured surface, roll the dough out into a large rectangle, about 1/4 inch thick.
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8. Brush the butter over the dough evenly. Mix the sugar and cinnamon together in a medium bowl and then sprinkle over the butter. Slice the dough into 12 pieces. Make 4 stacks of 3. Cut those in half, so that you have 24 pieces.
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9. Preheat the oven to 350u00b0F.
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10. Brush a loaf pan with a bit of melted butter (whatever is left in the melted butter pan). Put the stacks of bread in the loaf pan and squish them all in.
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11. Bake the bread at 350u00b0F for 35-40 minutes or until deep golden brown. Meanwhile, make the glaze: In a bowl, whisk together the powdered sugar, cream and maple extract until smooth.
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12. As soon as the pumpkin cinnamon bread comes out of the oven, gently ease the bread out of the loaf pan and drizzle them with glaze, which will melt over the hot bread. Serve immediately or at room temperature.
