Chill a mixing bowl and beaters in the freezer for 10 minutes. Pour the heavy whipping cream into the bowl and beat on medium speed until soft peaks form.
Add the sugar and vanilla extract. Continue beating until stiff peaks form, then stop to avoid over-whipping.
Spoon a thin layer of vanilla pudding into the bottom of a clear trifle dish or four individual glasses.
Add a layer of pound cake cubes over the pudding. Scatter one quarter of the candy corn on top.
Spread a layer of the whipped cream mixture over the candy corn. Repeat the pudding, cake, candy corn, and whipped cream layers once more, ending with whipped cream.
Finish with the remaining candy corn sprinkled across the top surface. Chill the trifle until ready to serve.