Sift together flour and 2 tablespoons confectioners' sugar in a bowl. Using a pastry blender or two knives, cut in 1 cup butter; knead until well blended. Form dough into 3/4 inch balls. Press evenly into 1 1/2 inch tart molds, pressing up the sides to form a shell. Bake in preheated oven until pale gold, about 16 minutes. Let shells cool in the pan. Gently loosen and remove them from pan using a knife.
Combine dates, orange juice, water, brown sugar, and salt in a saucepan. Bring to a gentle boil and cook for about 10 minutes, stirring constantly. Mash dates with a fork as they cook. Remove from heat and stir in vanilla. Allow mixture to cool before spooning into tart shells.
Cream 1/4 cup butter in a small bowl with an electric mixer. Gradually add 1 cup of the sugar while continuing to mix. Add the milk, remaining 1 1/4 cups sugar, and maple extract. Beat at high speed until smooth. Icing should be thick enough to pipe. Spoon mixture into pastry bag with a small round or star-shaped tip. Pipe a swirl of icing on each tart.