Preheat your oven to 375°F and line a large baking sheet (or two smaller ones) with parchment paper for easy cleanup.
Roll out the pie crusts on a clean surface. Use the rim of a mason jar lid or round cookie cutter to cut out circles. You’ll get about 9 circles from the two crusts, but if you gather and re-roll the scraps, you can make up to 12.
Place half of the pie crust circles onto your prepared baking sheet, spaced slightly apart.
Spoon a small amount of the chopped apple pie filling into the center of each circle, just enough to cover the middle without overflowing.
Gently press a party pick or popsicle stick into the filling, with one end sticking out like a lollipop handle. Then place a second pie crust circle on top of each filled base, lining it up with the bottom.
Use the tines of a fork to press around the edges, sealing the two crusts together and giving them that classic pie look.
Bake in the preheated oven for 20-22 minutes, or until the crust is golden brown and crisp.
While they cool slightly, whisk together the powdered sugar and milk to create a simple glaze. Drizzle it over the warm pie pops and let set before serving.
Serve and enjoy!