Place the cream cheese, heavy cream, and sugar in a mixing bowl and beat together until smooth using an electric mixer. Scrape the bowl and beat again. Slowly beat in the milk and vanilla until well combined.
Fill 12 popsicle molds 1⁄4 of the way full of the cheesecake mixture. Add a small spoonful with 1-2 cherries to each mold. Drop in a few pieces of crushed bear bite into each mold. Repeat this process until the popsicle molds are full. Insert popsicle sticks.
Sprinkle crushed bear bites at the base of each popsicle.
Use extra ingredients to make more popsicles, if desired.
Freeze for 8 hours.
To remove from molds: Run each popsicle mold under hot water until the popsicle easily releases.