Whip heavy cream in a bowl with vanilla extract to medium peaks.
Spoon a few tablespoons of raspberry pudding into a trifle dish or serving bowl.
Arrange a layer of vanilla wafer cookies on top, filling in the spaces with raspberries.
Stand a few vanilla wafers against the side for a pretty presentation.
Spoon half the remaining raspberry pudding over the first layer, then repeat with more wafer cookies and raspberries.
Top with whipped cream and sprinkle with crushed vanilla wafer cookies.
Refrigerate for a minimum of 4 hours or overnight before serving. Enjoy this chilled, delightful treat!