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Add blueberries and sugar to a small saucepan. Heat over medium heat, stirring occasionally, until blueberries start to release their juices and create a syrupy liquid. Remove from heat and cool.
Beat cream cheese and sugar in a large bowl until smooth. Add yogurt, milk, and vanilla extract. Beat again until combined.
In a separate bowl, combine graham cracker crumbs, melted butter, and sugar, stirring until moistened.
Fill each ice pop mold ¾ full by alternating with small spoonfuls of blueberry mixture and cream cheese mixture. Swirl with a skewer. Sprinkle graham cracker crumbs over top of each ice pop. Place a popsicle stick in the center of each mold.
Freeze for 4 hours or overnight before unmolding.