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In a saucepan over medium heat add the milk and espresso. Cook for 2 minutes.
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Add the pumpkin puree, pumpkin spice, cinnamon, sugar, and vanilla. Cook for 5 more minutes and stir until shiny.
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Remove from the fire and set aside to cool down for 5 minutes.
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Transfer to a blender, add the ice and blend until smooth.
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When ready to serve, drizzle some chocolate syrup in the glasses and pour the frozen milkshake into them.
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Top with whipped cream and chocolate syrup.
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Serve and enjoy.