Preheat oven to 350°F. Unfold phyllo sheets; place on a work surface. Cover with plastic wrap and a damp towel. Brush top side of 1 phyllo sheet lightly with butter. Top with a second sheet. Brush top side of second sheet lightly with butter. Repeat until stack is 6 sheets thick (do not brush top side of last sheet). Cut stack into 6 (about 4 ½-inch) squares. Repeat with remaining sheets and butter for a total of 12 squares. Press 1 phyllo square into each cup of a 12-cup muffin pan. Cover loosely with a damp paper towel while preparing the filling. 

Whisk together next 7 ingredients and ¾ teaspoon of the cinnamon in a bowl. Divide mixture among phyllo shells (about 4 ½ tablespoons each), and smooth tops. Bake in preheated oven until filling is almost set and phyllo is golden, 14 to 20 minutes. Cool on a wire rack 30 minutes. Remove from pan; chill 30 minutes or up to 2 days. 

Before serving, whisk together cream, maple syrup, vanilla, and remaining ¼ teaspoon cinnamon until stiff peaks form, 1 to 2 minutes. Transfer to a piping bag fitted with a small star tip. Pipe whipped cream onto each pie. Sprinkle with cinnamon.