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Break the cinnamon bark in half. Cut the peel off the orange and remove the pith from the inside of it. Break the orange into pieces. Put everything into a jar and add the cloves, star anise and vanilla.
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Pour the vodka into the jar and put the lid on it. Do not seal, but close the lid loosely.
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Fill a small saucepan with water approximately half way. Place the jar into the pan and turn the burner on medium-high. Allow the water to come to a simmer and remove the lid from the jar.
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Once the water has come to a simmer, the liquid will start to boil inside the jar. Let it cook like this for 10 minutes. Turn off the burner and let it cool 5 minutes.
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Remove the jar from the pan and transfer it to a hot pad to allow it to cool about 30 minutes.
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Strain the liquid from the bitters into a jar and close it with a lid.
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To make the manhattan, pour the whiskey, vermouth, and bitters into a cocktail shaker. Add ice, cover and shake until well mixed. Strain the cocktail into a glass.
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Add a maraschino cherry and an orange peel for garnish