In a mixing bowl, combine softened cream cheese, powdered sugar, and vanilla extract. Beat on medium speed until smooth.
In a separate bowl, whip the heavy cream until stiff peaks form.
Gently fold the cream cheese mixture into the whipped cream until combined.
Mix pumpkin puree with pumpkin pie spice and fold into the cream mixture until well integrated.
Layer crushed Oreo cookies at the bottom of dessert glasses, then add layers of pumpkin cheesecake filling and vanilla cheesecake filling until filled.
Sprinkle pumpkin pie spice on top and add optional pumpkin candies for garnish.
Refrigerate for at least 3 hours or until set before serving.
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Notes
Store leftovers in the refrigerator for up to 5 days.