Cranberry sauce: In a small saucepan over medium heat, combine cranberries, sugar, and orange extract. Bring to a boil, then reduce heat and simmer until slightly reduced, about 10 minutes. Let cool to room temperature.
Crust: In a food processor, finely crush graham crackers. Add melted butter and sugar, blending until moistened. Press the mixture onto the bottom of a greased 9-inch springform pan. Spread half of the cranberry sauce over the crust. Freeze while preparing the filling.
Cheesecake filling: In a medium bowl, mix cream cheese and powdered sugar until smooth. In a separate bowl, whip heavy cream to soft peaks, add vanilla and orange extract, and a few drops of orange food coloring until stiff peaks form. Combine with cream cheese mixture on low speed. Spoon over the cranberry layer in the crust. Refrigerate for at least 6 hours, or overnight.
Topping: Mix whipped cream with orange food coloring. Once set, run a thin knife around the edges of the cheesecake to loosen, remove the sides of the springform pan, spread remaining cranberry sauce in the center, and pipe the colored whipped cream around the edges.