In a chilled metal bowl, mix ice cream,peppermint extract and food coloring. Refreezeice cream at least 2 hours or up to 3 days. Ina microwave-safe bowl, microwave chocolateand milk in 10-second intervals, stirring aftereach interval, until chocolate melts. Chillchocolate sauce until ready to use (up to3 days); to reheat, microwave for 10 seconds.
Pour half of chocolate sauce evenly amongfour 5-ounce serving glasses; scoop one quarterof ice cream into each glass; pour remaininghalf of chocolate sauce over ice cream.
Garnishwith pizzelle halves and candy canes; serve.