Twist open the Oreo cookies and scrape out the cream filling. Slice large berries into smaller pieces and set aside.
Combine cream cheese and powdered sugar and mix until smooth.
Add heavy cream and vanilla extract to the cream cheese mixture. Whip until it’s thick and holds firm peaks.
Fill a piping bag with the cream mixture and start layering the cream, cookies, and berries in small glasses or jars.
Continue alternating the layers until you’ve filled the glasses.
Top the mini cakes with chocolate shavings, fresh fruit, and a mini Oreo!