In a large mixing bowl, whip the heavy cream until soft peaks form.
Gradually add the powdered sugar and vanilla extract, continuing to whip until stiff peaks form.
In a trifle dish or large glass bowl, layer half of the crushed Oreo cookies on the bottom.
Spread half of the whipped cream mixture over the cookies, followed by half of the vanilla pudding.
Add a layer of sliced strawberries and blueberries.
Repeat the layers with the remaining Oreo cookies, whipped cream, pudding, and top with the remaining strawberries and blueberries.
Chill the trifle in the refrigerator for at least 2 hours before serving to allow the flavors to meld.