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In a small saucepan, heat milk over med heat until it begins to simmer (about 2-3 minutes), stirring occasionally.
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Turn heat to low, and add in pumpkin puree, maple syrup, brown sugar, cinnamon, nutmeg, all spice, and vanilla extract, whisking gently until all ingredients are combined.
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While the stove is still on low, add in chopped chocolate, and whisk until the chocolate is melted.
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Divide hot chocolate between 3-4 glasses, and top with whipped cream and cinnamon.
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Enjoy!