This recipe will make about 8 cups. Work in batches to best fit your blender.
Place a medium bowl (preferably metal) in the freezer to chill, 2-3 minutes.
Once the bowl is chilled, remove from the freezer. Measure cold cream, sugar, and vanilla into the bowl.
8 fl oz (1 cup) heavy cream
2 tsp granulated sugar
1 tsp vanilla extract
Use a whisk (or hand blender) to beat the cream vigorously, until medium-soft peaks form, about 3 minutes if whisking. (For medium-soft peaks, when you pull the whisk out of the bowl, the cream should hold its shape, with a peak that curls over slightly.) Set aside.
Place ice cream, milk, cocoa powder, and cherries in a blender. Blend on high until smooth.
32 fl oz (4 cups) vanilla ice cream
16 fl oz (2 cups) whole milk
2 tbsp cocoa powder
1 cup frozen cherries
To serve, divide milkshake between glasses, top with whipped cream, and enjoy!