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Prepare the Strawberries: Rinse the strawberries and pat them completely dry. Carefully slice off the green leaves (the hull) from the top. For a stable base, slice a very thin piece off the bottom of each berry so it can stand upright without tipping over.
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Hollow the Berries: Using a small melon baller, a small measuring spoon, or a paring knife, carefully scoop out the center core of each strawberry to create a small cavity. Be careful not to puncture the sides or bottom. Arrange the hollowed strawberries on a serving platter or baking sheet.
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Make the Cheesecake Filling: In a medium mixing bowl, beat the softened cream cheese with a hand mixer on medium speed until it is completely smooth and creamy. Add the heavy cream and beat until the mixture is light and well combined. Beat in the confectioners’ sugar and vanilla extract until the filling is smooth and fluffy.
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Fill the Strawberries: Spoon the cheesecake filling into a piping bag fitted with a star or round tip (for a pretty look) or simply into a plastic zip-top bag with a corner snipped off. Gently pipe the filling into each strawberry, swirling it slightly above the top for an elegant finish. Alternatively, you can carefully spoon the filling into each berry.
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Garnish and Serve: Just before serving, sprinkle the filled strawberries with crushed graham crackers and your choice of mini chocolate chips or chocolate shavings. For the best texture, serve immediately or refrigerate for up to 2 hours.
Chef’s Tip: For the neatest presentation, wait to garnish the strawberries until right before you serve them. This keeps the graham cracker crumbs from getting soft.
