In the bowl of your stand mixer (or using a hand mixer) whip the cream cheese until it's creamy and smooth.
Beat in the powdered sugar until it's completely combined, scraping down the sides of the bowl a few times.
Add in the whole milk slowly, continuing to beat the mixture until it's smooth and very liquidy.
Add the thawed cherries to a separate bowl and mash them well until the mixture is liquidy with some cherry chunks remaining. I like making these popsicles with chunks of cherries and for this result, mashing is the way to go. If you'd prefer a smooth texture throughout the popsicles, feel free to puree the cherries.
Layer the cream cheese mixture and the cherry mixture into a 10-popsicle mold and put them in the freezer until they're completely frozen (overnight is best).
Remove from the molds once they're completely frozen and enjoy immediately!