Start by whipping heavy cream in a chilled bowl using an electric mixer on high speed until stiff peaks form, about 3-5 minutes. Dip the rims of glasses in maple syrup and roll in black sanding sugar.

In a high-speed blender, combine the milkshake ingredients: vanilla ice cream, milk, black cocoa powder, maple syrup, and vanilla extract. Blend on medium-high for about 30 seconds until silky smooth.

Taste your mixture. Add more black cocoa powder or maple syrup for desired intensity and blend briefly to combine.

Pour the milkshake into prepared glasses and top each with whipped cream.

Serve immediately for the best texture and flavor.