Cut "lid" from stem end of each orange; discard lids. With spoon or fingers, scoop and scrape out flesh from each orange to within 1/4 inch of peel, being careful not to puncture peel. Reserve orange flesh for another use. Place orange shells on cookie sheet or tray.
In small saucepan, combine 1 cup of the apple juice and cinnamon candies. Cook over medium-high heat until mixture comes to a boil and candies melt, stirring constantly. Remove from heat. Add gelatin; stir at least 2 minutes or until completely dissolved. Stir in remaining 1 cup cold apple juice. Pour evenly into orange shells. Refrigerate 4 hours.
With small sharp knife, cut out jack-o'-lantern features into side of each orange. Carefully remove peel to reveal gelatin under features. (If gelatin does not release well, rinse paper towel in hot water and wring out; press hot towel on features to soften gelatin slightly, then remove peel.)
To serve, top each dessert with dollop of whipped topping. If desired, sprinkle with cinnamon.