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In the bowl of a stand mixer and using the whisk attachment, whip heavy cream until soft peaks form (this will take between five and 10 minutes). Start on low speed and gradually increase speed to high. Place whipped cream in a medium-sized bowl and set aside.
In the bowl of a stand mixer and using the paddle attachment, mix cream cheese, sugar, salt, and vanilla extract on low speed until well combined.
Gently fold whipped cream into the cream cheese mixture until well combined. Refrigerate until ready to use.
In a medium-sized saucepan, bring milk and sugar to simmer on medium-low heat, stirring until sugar is dissolved.
Remove from heat and whisk in chocolate chips until melted.
Stir in food coloring and vanilla extract.
Pour into mugs and top with cream cheese whipped cream, then put in a candy cane as a stirrer for a sweet finishing touch.