1 1/2 cups strong hot brewed coffee
3 tablespoons packed light brown sugar
1 1/2 tablespoons chocolate syrup, such as Hershey’s
1 cup ice cold milk
1/4 teaspoon vanilla extract
Handful or so crushed ice
Lightly sweetened whipped cream, for garnish
1 small piece semisweet or bittersweet chocolate, for garnish
Combine the hot coffee and brown sugar in a large measuring cup and stir until the brown sugar dissolves. Remove from the heat and stir in the chocolate syrup. Transfer to a shallow bowl. Cool briefly at room temperature, then chill until ice cold. You can accelerate this step by putting it in the freezer, but just make sure it doesn’t start to ice.
Combine the chilled coffee, milk, and vanilla in a small pitcher; stir to blend. Divide the coffee between 2 serving glasses, adding a small handful of crushed ice to each. Top each glass with whipped cream then grate a little chocolate over each one.