Press four marshmallows onto a straw, wooden skewer or treat stick with a twisting motion. Set aside on waxed paper.
Add caramel and whipping cream to a microwave-safe bowl. Melt the caramel in the microwave according to package directions giving special care not to overheat the candy.
Pour caramel over the marshmallows, coating completely and allowing the excess to run back into the bowl.
Roll the coated marshmallows in chopped peanuts. Place marshmallow pop on waxed paper until set.
Melt the milk chocolate in the microwave according to package directions giving special care not to overheat the candy. If the candy is overheated, it will be too thick. You can add 1 teaspoon of vegetable shortening or coconut oil to help thin the chocolate but do not add any other type of liquid as the candy will seize and harden.
Pour chocolate over the marshmallows, coating completely and allowing the excess to run back into the bowl. Place on waxed paper and refrigerate until set.
Transfer remaining melted milk chocolate to a piping bag or zip-top freezer bag. Snip the corner of the bag and drizzle melted candy over the marshmallows. Allow the marshmallows to rest on waxed paper until set before packaging or serving.
Serve immediately, or within a few days. Best if stored in an airtight container in the refrigerator.