Prep the baking sheet: Line a baking sheet with parchment paper. Set toppings in small bowls so they’re ready for decorating.
Slice and dry the apples: Wash, dry, and slice apples into ½-inch to ¾-inch slices. Remove seeds and core pieces, then pat each slice very dry with paper towels.
Add the sticks: Push a popsicle stick halfway into the bottom of each apple slice. If needed, make a small slit first to prevent splitting.
Melt and dip: Melt chocolate in 20- to 30-second intervals, stirring until smooth. Dip each apple slice in chocolate, let excess drip off, then place on the lined baking sheet.
Chill the chocolate: Refrigerate for 5 to 10 minutes, or until the chocolate feels firm.
Melt and drizzle caramel: Melt soft caramels with cream or milk in short intervals, stirring until smooth. Let cool for about 5 minutes, then drizzle over the chocolate-coated apples.
Decorate and serve: Add toppings while the caramel is sticky. Chill for 10 to 15 minutes, then serve cold or slightly chilled the same day.