Finely crush the graham crackers in a resealable plastic bag with a rolling pin until they resemble small crumbs. Set aside in a small bowl.
Whisk together the milk, liqueur and instant pudding in a medium bowl until the pudding thickens and begins to set, about 5 minutes.
With a stand mixer or an electric hand mixer, beat together the heavy cream, confectioners' sugar and cream cheese on medium speed until light and fluffy and soft peaks begin to form, about 2 minutes. Add the pudding to the cream cheese mixture and fold to combine.
To assemble, fill a resealable plastic bag with the pudding mixture and cut a small hole at one end. Add 2 tablespoons graham cracker crumbs in an even layer at the bottom of 6 individual cups. Top with a scant 1/4 cup pudding mixture, another layer of graham cracker crumbs, another scant 1/4 cup pudding and a final layer of graham cracker crumbs. Refrigerate until ready to serve. Garnish with an orange slice and maraschino cherry in each cup before serving.