Prep the fruit: Rinse and dry berries well. Slice strawberries.
Set aside.
Make the cream layer: In a large bowl, beat the softened cream cheese until smooth (about 30–45 seconds). Add cold heavy cream, powdered sugar, and vanilla. Beat on medium-high until stiff peaks form, 2–3 minutes.
Don’t overmix.
Test your Oreos: If they’re very fresh and crisp, you can lightly dip each cookie in milk for 1 second per side. This helps soften faster. If not, skip the dip—the cream will do the work.
First layer of cookies: Arrange a snug layer of Oreos across the bottom of the dish.
Break a few to fill gaps.
Add cream: Spread about one-third of the whipped cream mixture over the cookies in an even layer.
Red and blue layer: Scatter a layer of sliced strawberries and some blueberries over the cream.
Repeat: Add another layer of Oreos, another third of the cream, and more berries.
Final layer: Add a final layer of Oreos and top with the remaining cream. Smooth the top.
Decorate: Arrange strawberries and blueberries in a simple flag pattern or in stripes for a festive look.
Chill: Cover and refrigerate for at least 4 hours, preferably overnight. The cookies soften and the flavors meld.
Serve: Slice with a sharp knife or a spatula.
Wipe the blade between cuts for clean squares.