Add the cream cheese and powdered sugar into a large mixing bowl and beat with an electric hand mixer until well combined. Add in the milk, whipping cream, and vanilla extract and continue mixing on low speed until all well incorporated.
Place 2-3 cherries, along with some of the syrup, at the bottom of each popsicle mold, then fill about halfway with some of cheesecake mixture.
Add a few more cherries, and then continue to fill with remaining mixture. Leave some room at the top to add a few more cherries.
Place in freezer for about 1 hour. Then remove to add your popsicle sticks.
Place back into freezer for at least 5 hours or until solid.
Run under warm water, if necessary, to release from molds when ready to eat.