For the Crust:
To start, gather your ingredients and line your cupcake pan(s). For the crust, crush the Oreos into fine crumbs. Mix the crumbs with ½ cup of melted butter until it resembles wet sand.
Press a loose tablespoon's worth of the crumb mixture into each lined cupcake cavity, creating a firm base for your cheesecakes.
For the Filling:
In the bowl of a stand mixer, combine 16 oz of softened cream cheese with ½ cup of sugar until smooth and free of lumps. Add 1 cup of heavy whipping cream and 1 teaspoon of peppermint flavoring plus 1 teaspoon of vanilla extract. Mix thoroughly, ensuring a creamy consistency.
Divide the filling among the crust-filled liners, smoothing the tops in line with the pan. Chill for several hours preferably overnight, to allow to set.
Peppermint Chocolate Ganache:
For the decadent ganache, combine 1 cup of semi-sweet or dark chocolate chips, 4 tablespoons of heavy cream, and 1/2 teaspoon of peppermint flavoring (the latter is optional if you prefer a lighter peppermint flavor).
Heat in 30-second increments, stirring until smooth. Set aside to cool slightly.
For the Whipped Cream:
In a separate bowl, combine the remaining ½ cup of heavy cream and 2 tablespoons of powdered sugar in a stand mixer. Mix on medium/high for 2-3 minutes or until stiff peaks form. Transfer the whipped cream to a piping bag fitted with a large star tip.
To Assemble:
Once the cheesecakes are chilled and set, it's time to decorate! Spoon about a tablespoon of peppermint chocolate ganache onto each cheesecake, spreading it evenly to just inside the edges. Alternatively, if you find it easier to do - simply drizzle just enough chocolate over the cheesecake.
Pipe a small dollop of whipped cream on top.
Finish by sprinkling crushed peppermint pieces for an extra festive touch.