Chocolate Milk Punch Pops are the sort of treat guests will rave about for years to come. In these popsicles, the punch is bourbon-based, but the chocolate milk and vanilla make for a smooth indulgence.
Combine chocolate milk, bourbon, sugar, vanilla, and nutmeg in a 2-qt. measuring cup, stirring until sugar dissolves. Pour half of mixture into paper cups; cover and chill remaining half.
Cover each cup with aluminum foil; make a small slit in center, and insert 1 ice-cream spoon into each cup. Freeze 4 hours or until firm.
Carefully remove foil from cups. Pour 1 Tbsp. chocolate syrup into each cup; freeze, uncovered, 2 hours. Pour remaining milk mixture into cups; freeze, uncovered, 8 hours or until firm.