Place the softened cream cheese in a mixing bowl and beat it until smooth.
Add the powdered sugar, orange zest, and vanilla extract to the bowl and mix until fully combined and creamy.
Spoon the orange creamsicle dip into a small bowl and set it in the center of a large serving board.
Arrange the candy corn in small piles around the dip to create color blocks.
Place the clementine segments in clusters next to the candy corn.
Fan the vanilla wafers along the edges of the board for easy grabbing.
Tuck the black licorice pieces near the clementines to add contrast and a jack-o'-lantern accent.