Place 4 heavy pint glasses in the freezer to chill for 30 minutes. Add the ice cream, milk, ice cubes, bourbon and 4 tablespoons of the chocolate syrup to a powerful blender. Blend until smooth. (A good milk shake should be eaten with a spoon—so if the mixture seems too thin, add another .25 to .5 cup ice cream and blend again.) Divide evenly among the prepared glasses and top each with .5 tablespoon of the remaining chocolate syrup. Serve immediately.
*Simple Chocolate Syrup
Whisk together the cocoa powder and water in a medium saucepan over medium heat until fully dissolved. Whisk in the sugar and increase the heat to medium-high. Boil the mixture for about 3 minutes, then reduce the heat to low and simmer for another 1 to 2 minutes. Remove from the heat and stir in the salt. Let cool to room temperature and store tightly covered in the refrigerator for up to 3 weeks.
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