Combine the first 4 ingredients in a medium saucepan, and bring to a boil. Cover, reduce heat, and simmer 5 minutes. Uncover; simmer 5 minutes or until tender, stirring occasionally. Spoon into a bowl; cover and chill.
Spoon 1 tablespoon cookie crumbs into each of 8 (8-ounce) glasses; top each with 1/4 cup apple mixture and 3 tablespoons ice cream. Repeat the layers once, ending with ice cream. Serve immediately.