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In a large bowl, stir together the flour, 1⁄4 cup of the brown sugar, the baking powder, cinnamon, ginger, allspice, and salt. Set aside. In a small bowl, stir together the milk, pumpkin puree, oil, and vanilla extract, and set aside.
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In another bowl, using an electric mixer on high speed, beat together the eggs and the remaining 1 tablespoon brown sugar until the mixture is very thick, fluffy, and pale, about 5 minutes. Stir the reserved milk mixture into the flour mixture until just incorporated. Then, gently fold in the beaten egg mixture until completely incorporated. Let the batter rest, covered, at room temperature for about 30 minutes. Meanwhile, preheat your waffle iron according to the manufacturer’s instructions.
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Spray the grates of the waffle iron with cooking spray and cook the waffles according to the manufacturer’s instructions. I use a high heat setting, and cook the waffles until deep golden brown, 5 to 6 minutes.
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Serve with whipped cream, cinnamon, and syrup.